When Worlds Collide
by AlexJohnD
Summary: Ever since his mother passed, Hiccup's life has been miserable and boring, mostly thanks to his father. But that changes when a high up mob member takes an interest in him. Rated T because I've never done this before and I'm paranoid. AU. Toothcup, yes they are both guys, don't like don't read. Cover art by Warrior Nun
1. Chapter 1

**Hey everyone, thanks for stopping by! So yes this is a Toothcup fic, however it will NOT be rated M for those of you wondering. I have a hard enough time writing normally, so I'm not even considering throwing that into the mix. However I reserve the right to imply it at any time. Actually the only reason I'm writing this at all is because of ADAMalchemist. So if you like it, go thank him for kicking me in the pants and getting me to write this. If you hate it, you have my permission to throw rotten tomatoes at him XD. Sorry Adam 3. **

**I'm sorry to extend this A/N further, but there are just a few more things I need to say. First, in this fic, Stoick will not be a …..nice…character. He will be a bad person. While I know many people disagree with this (I'm one of them too) I am doing this because it is important to my story. Plus this is an AU so characters don't really have to be like they are in canon, because otherwise it wouldn't be an AU! In fact, I would say most (if not all) characters in this story are OOC. I mean, the teens from the book are going to be involved with illegal gangs, and Hiccup is gay. If you have a problem with that, the back button is in the top left corner of most internet browsers. Finally, I am stating now that if I have any supporters, I promise to finish this fic. I can't say when, but it will be finished within a decent time frame. Feel free to see my commitment rant on my profile. **

**OK, finally onwards!**

The sun broke through the gap in the curtains of Hiccup Haddock's room early on Thursday morning. The light splashed across the pale green walls and over the face of the sleeping teen, resting right over his eyes and rousing him from his slumber. As he sat up in his bed he took a good look around his bedroom. His gaze shifted to his desk, crowded with school papers, clothes, and other miscellaneous items, then over to the mirror on his dresser. His room was by no means big, but it was decently sized considering it was in the cramped condo he lived in with his father.

The 19 year old finally stood from his bed and nearly stumbled over his own two feet several times as he made his way to the bathroom. When he finally arrived, he clung to the sink like his life depended on it as he stared into the mirror.

"This is definitely the worst day of the week," Hiccup said to his reflection as he fumbled for his toothbrush. While he hated most days he had to wake up early to get to classes at New York University, he hated Thursdays the most because he had to be there 8am to 8pm. At least he could look forward to his two favourite courses today: Northern European History and History of Organized Crime. An odd combination of interests to most, but not that it mattered.

Hiccup didn't have any friends. He had his father to thank for that. Ever since Hiccup had come out to his father (and to this day he still wasn't sure WHY he had), Stoick had been on his case. Hiccup found out the hard way that Stoick was homophobic, so any guy Hiccup would try to be around would be scared off by his father, and the same with any girls because since Hiccup didn't want to be with one romantically, he shouldn't be with them at all. Hiccup tried keeping secret friends, but Stoick would just use his connections down at the police station and find out, so Hiccup just stopped trying. He had a feeling that if his mother was still around she would be a lot more understanding.

Hiccup finished up in the bathroom before heading back to his room, throwing on his favourite green shirt and a pair of blue jeans before heading to the kitchen. Not a very far trek considering the apartment was only around 800 square feet. The door to his bedroom, his father's bedroom, and the bathroom were in a little section just off the living room which was attached to the kitchen. Hiccup's room was the only room in the condo that had been painted. Every other wall was still the same plain white from when they bought the place. And Hiccup's room was only painted because he did it himself.

There was a time back when Hiccup's mother was alive where they had lived in a nice house on Long Island. It wasn't huge, but a comfortable size for the three of them. After she passed Stoick moved them into the condo, claiming it was because he didn't want to live in the house where his wife had died anymore. Hiccup knew that was completely untrue, that his father just wanted the money for his "after work activities".

When Hiccup walked into the kitchen he saw his father sitting at the table reading the morning paper. To say Stoick was a large man would be an understatement. The man was over seven feet tall and 400 pounds. And that was mostly muscle too, which made it even easier to scare off Hiccup's attempts at friends. You know, in case his position at the police department wasn't enough.

"Morning dad," Hiccup said, a little lacklustre knowing that he probably wouldn't get a coherent response. His suspicions were confirmed when all he got back was a grumble. While normally their morning conversation ended there, Hiccup decided to take another step that morning.

"So I was thinking I would take the subway to school today," Hiccup started as he poured his favourite cereal into a bowl.

"Absolutely not," Stoick said in response, not even looking up from his newspaper.

"Why?" Hiccup asked, reaching for the milk in the fridge. "It would be faster than having Gobber drive me with all the traffic."

"Wouldn't be safe for someone like you," was all Hiccup got in response. Now to some that may seem slightly like concern for their child, but Hiccup knew it as the thinly veiled insult it was. But not wanting to start an argument again, he let the subject drop.

They sat in silence for the next several minutes, the only sound being the crunching of Hiccup's cereal as he chewed and the sounds of the city outside their window. It was Stoick who finally broke the silence.

"I'm going to work now, I won't be back until late, Gobber will be waiting for you downstairs soon."

"You're going to be late again?" Hiccup asked as his father reached for his hat. "Why is it today?"

"Work, like always. The members of the Fire Breathers gang aren't going to catch themselves you know," Stoick replied, half out the front door.

"Liar," Hiccup mumbled after he was sure his father was out of earshot. He knew what his father did after work every day. At first Hiccup had been naïve, thinking it actually was work. But then one day back before he had come out but after his mom had died (a time when they actually had an okay relationship for a while), Hiccup had gone into the station to surprise his father with his favourite doughnuts, only to find that he had been gone for hours. Another cop at the station that didn't know it was a secret from Hiccup told him that Stoick had gone out with a few other officers like he did most days after his shift. Hiccup tried not to think about it because it just made him upset.

It only took Hiccup a few more minutes to finish off his bowl of cereal. He placed his bowl in the sink for later and grabbed his knapsack before heading out the door. After locking it, he turned down the hallway towards the elevators. It never ceased to confuse Hiccup as to why a fourty story building only had two elevators. However, seeing as he was on the twenty-seventh of fourty floors, he could generally get into the first elevator that came, but it would be crowded at this hour. Sure enough when the elevator came he managed to just barely squeeze himself in, but even though it was full it still stopped at every other floor on the way down with other people trying to get on. It was going to be a long morning.

* * *

When Hiccup finally got down to the lobby with everyone else in the elevator, he walked with the herd across the lobby and out the front doors. He immediately started searching for the car that was going to give him a lift to school. After a moment of searching the countless cars and attempting to look over the numerous pedestrians' heads, he finally saw Gobber pull up to the curb in the all black 2002 Lincoln Continental. Hiccup had to admit, sometimes the fact that Stoick made a smack-ton of money as the NYPD's head detective had its benefits. The car came in quite useful sometimes. This was not one of them however, as the subway really would be faster. Fortunately Hiccup didn't mind the driver.

"So, another lovely morning conversation with your father I assume?" Gobber asked in his thick accent after navigating away from the curb. Gobber was also a large man, but not quite as tall as Stoick. That was probably a good thing or he may not have been able to fit comfortably into the car for long periods of time. He had blonde hair, but he was balding at the top and had a mustache so long you could strangle him with it. That is, if you could get close enough to him without him knocking you off your feet with his strength.

"Yeah, it was real interesting," Hiccup responded, his voice laced with sarcasm. "He told me he was going to be working late again tonight. I'm assuming that means the usual tonight for him then?"

"You know I can't answer that, Hiccup," Gobber said. And Hiccup knew he was right. Gobber didn't want to lose his job, and that meant following orders and not telling Hiccup of Stoick's "travels". It was also why Hiccup actually took the car each morning instead of sneaking onto the subway; if his dad found out he would probably fire Gobber. Hiccup couldn't be responsible for that.

"Yeah, yeah," Hiccup said as he stared out the window, watching himself get nowhere fast in Manhattan traffic. He had started following a pedestrian with his eyes to see if she would beat them to the next intersection.

"So, today you have your Northern European History class, right?" This simple question perked Hiccup right up.

"Yeah, it's my first class."

"You should be acing that course, it is your bloodline you know."

"Just because I have a Scandinavian background doesn't mean I know the whole history, Gobber," Hiccup replied, smirking. Gobber had the same background as Hiccup and his parents, and he was quite proud of his background. It was actually Gobber that got Hiccup interested in his background and history.

"Well then start paying better attention in class!" Gobber said chuckling. "At least that's more relevant than that other course you're so interested in. The criminals one or whatever that is."

"A History of Organized Crime," Hiccup corrected, "and it's actually quite interesting. Studying mobs and gangs and stuff like that. It's cool."

"Ah," Gobber scoffed, "when are you ever going to use that?"

"Well I'd like to point out that it is kind of what my father is doing at work. We are actually studying the Fire Breathers gang a little. And besides, it's definitely more useful than the Northern European History class," Hiccup stated.

"Bah, you don't know what you're talking about, one day you'll see. You'll see that you should have taken even more courses on your history rather than this silly mob junk. Knowing the history could win you a million dollars or something! Or someone may challenge you to a trivia honour contest!"

"I'll take my chances," Hiccup replied dryly. They sat in silence for a few more minutes, Gobber focusing on weaving through the traffic, before he finally had to come to another full stop at West 4th Street. Hiccup finally realized why the traffic had been especially bad today; there was an accident at Broadway and West 3rd Street. Hiccup decided this was as good a time as any to take his leave. "You can just let me off here, I can walk it."

"Are you sure? We are at the wrong end of campus for your first class."

"Yeah, it's okay. Besides," Hiccup started as he opened the door, "my class starts in five minutes. I know I can walk the distance in five minutes. With this traffic I am highly doubtful you can drive it in that amount of time. Besides, we wouldn't want me missing a minute of history, would we?"

Hiccup didn't even give Gobber a chance to answer. He just gave him a wink, slammed the door, and ran off through the heart of campus. At least Hiccup had his classes and Gobber to keep his life interesting.

**Alright everyone, that's it for chapter one. Normally this is where some people would ask if they should continue, but we haven't even seen Toothless yet. So I'm going to ask that question after chapter 2. The reason I divided it into 2 chapters is because IF I do continue (and I will as long as I have someone who wants me to), this is about how long the chapters will probably be. Don't want to get anyone's hopes up with long chapters at the beginning when they probably won't be later on.**

**Till next time! And please review! I even want the bad reviews (especially if they tell me why this was so bad in a non-insulting way)!**


	2. Chapter 2

**A/N: Hey everyone, I'm back with chapter 2. So at the end of this chapter if you would be so kind as to review and tell whether or not you care if this story is continued that would be great. I find no point in continuing if absolutely no one wants to read it anyways. **

**Oh, and I'd like to thank Doomsday BeamXD, The-Fantastic-Story-Writer, Guest, and Izzywing for their reviews, and ADAMalchemist for his support and making sure whatever I post isn't just awful.**

**Also, in case it wasn't already extremely obvious, I am not Cressida Cowell nor and I Dreamworks, so I do not own these characters. Just feel like I should put that at least once…..**

* * *

Hiccup glanced down at his watch as he ran through the building, shoes hitting the ground and echoing with each step, and sweat starting to bead on his forehead. 7:59am. He had one minute to get to class before the professor would lock the door on him. He needed to get to room 526, but he was only at 507. Fortunately he didn't have to worry about dodging other people as the narrow hallway was deserted.

'_Come on, come on!' _Hiccup thought to himself as he used his last bit of morning energy to add a little burst of extra speed and literally slide through the doorway as his professor was about to close and lock it.

"Impressive form Mr. Haddock," Professor Jacobs said with a smile. "However perhaps leaving the house a few minutes earlier would be easier? Unless you enjoy a little anxiety with your cardio, or enjoy performing your rendition of the electric slide?"

Hiccup couldn't help but chuckle. Professor Jacobs was strict but amusing. He was one of the reasons that Hiccup loved this course so much. You know, other than the material. And speaking of the material, Hiccup perked up even more when he heard what they would be covering today.

Hiccup was walking to his seat in the back row when Professor Jacobs stated, "and today, class, we will be covering the Viking period. Now, who can tell me the time period during which the Vikings lived?"

* * *

Class continued on as usual. And as usual, Hiccup was the only one who had done any of the readings, so he was the one answering most of the questions. In the end the two hours passed a little faster than he would have liked. Especially now that he couldn't look forward to a class he would like until the end of the day. Well, a class he liked for the material anyways.

Next up Hiccup had to get half way across campus to his Design Studio class. While Hiccup technically did choose architecture for himself, he really didn't have much of a choice. His mother had made his father promise to make sure he got a post-secondary education (probably the only reason Stoick was paying for it in the first place), but Stoick had told Hiccup he would only pay for a degree he considered respectable. Hiccup considered just not getting a degree, but he didn't want to go against his mother's wishes, and he definitely couldn't afford a degree himself. Hiccup chose architecture because it seemed the least boring to him. Plus it gave him a chance to work his creative muscle a little.

Design studio was the closest thing that Hiccup generally got to social interaction with people around his age, since a lot of the time it was group work. Hiccup had to admit though, while he generally wasn't a fan of group work, this group assignment wasn't as bad as the others, mostly because he had Jason Anderson as his partner. Jason was tall, had blonde, medium length hair, and muscles that weren't obscenely large but not small enough that you could miss them if you weren't looking. Basically, to Hiccup, he was _really _good looking. Whenever Hiccup saw him he had to put extra effort into making sure he didn't turn into a puddle of blubbering mush with a face brighter than a stop sign.

Hiccup sat down at his drafting table and within a few seconds Jason had taken the seat next to him.

"Hey Hiccup. I brought the drafting paper today so that we can get started on the basic design. I don't know about you, but I'm really excited to get started on this," Jason said, grinning from ear to ear.

Since they were first years the assignment wasn't too hard. Design the layout and exterior of a simple single family home. The requirements included a two car attached garage, either three or four bedrooms, at least two bathrooms, and a finished basement. Anything else was left up to the students. Normally Hiccup wouldn't care and would let his partner do all the work since his designing preferences lay with smaller gadgets and inventions rather than full blown architecture, however Jason LOVED architecture and Hiccup desperately wanted to be on his good side.

"Great, so why don't we do a little brainstorming first?" Hiccup asked, trying to hide the dreaminess in his voice as best he could.

"Great idea! So I was thinking a basic bungalow, but since there were no restrictions on the lot size, I was thinking we could try something cool by putting the garage in the back and having the driveway loop around the house."

"Interesting ideas," Hiccup said, "but what about this." Hiccup knew he couldn't just agree with absolutely everything Jason said; that might arouse suspicion. He grabbed a pencil and started a rough sketch. "I was thinking something a little grander, especially if you were going to do something as unique as the garage at the back. What if we did a two story house, with a front balcony and a balcony on the second level right above it as well," Hiccup suggested. "That way the front of the house looks really nice and gives an even better reason to have the garage at the back."

"Actually, I really like that idea," Jason replied while stroking his chin. "But the balcony on the second level, how is it going to be supported?"

"With columns here," Hiccup started while drawing in a quick column, "and here."

"That looks amazing Hiccup, you're incredible!" Jason said whole looking over the rough sketch. "But since we are going to keep the garage at the back actually I think we should keep the front yard really small by placing the house close to the curb. Otherwise the driveway will be insanely long."

Hiccup had stopped paying attention after the "you're incredible!" He probably wouldn't have been able to hear anything anyways since most of his energy went into making sure his face didn't look like a tomato from the compliment, or at least hiding it from Jason. It took him a few minutes before he was sure all the heat had left his face, and in that entire period of time all he had been giving to Jason was affirmative mumbles every now and again even though he had no idea what he was saying.

'_Way to possibly blow it,_' Hiccup thought to himself. For all Hiccup knew Jason could have just said that they should turn it into a condo complex or actually build a model and blow it up with dynamite.

The class continued on and by the time the class ended it was 2pm. Why the studio was four hours long when all they did was work on assignments that were given in thirty seconds was a mystery to Hiccup. But part of their mark was attendance for the WHOLE period, so he stayed every time. At least he and Jason got pretty much the whole assignment done. Jason had agreed to take it home and put on the finishing touches.

Between 2 and 6pm was Hiccup's massive gap in his schedule. He knew he could go home, but what would the point be? There was nothing for him to do there and all it meant was running the risk of bumping into his father and having yet another awkward conversation. So Hiccup did what he always did during this gap; he went to the nearest McDonalds, had a late lunch, and walked around lower Manhattan.

* * *

It was 5:30 when Hiccup walked into the classroom that would hold his History of Organized Crime class at 6. His walk had been the same as always, boring and uneventful. Well, as uneventful as lower Manhattan can be at the beginning and middle of the afternoon rush. To most it would have been plenty exciting with all the people and cars around, but Hiccup had seen it all before. Kind of like how he got no thrill when he saw the Empire State Building or the Statue of Liberty or any of those other buildings the tourists all fawned over.

Hiccup just doodled on some spare paper as the rest of the class and eventually the professor came in. Once again it was Professor Jacobs, possibly the only other person on the planet that had an interest in the histories of both northern Europe and organized crime. Yes they were both history, but those two exact subjects? What were the odds?

After Professor Jacobs put down his bag, he walked over to the door and started staring at his watch. Sure enough, the second the clock hit 6 o'clock the door was shut and locked. The professor hadn't walked two steps before all anyone in the room heard was the sound of a body crashing into the door and some muffled foul language coming from the other side.

Professor Jacobs, unfazed by the incident, simply glanced at the door then turned to Hiccup and said, "well Haddock, that was almost you this morning, wasn't it?"

Hiccup couldn't help but smile, and that smile only grew larger again when Professor Jacobs said that he had some newspaper articles on the Fire Breathers gang that they would be looking at.

* * *

8 o'clock rolled around, and Hiccup's day of classes drew to a close. As he packed up his books, he glanced down at his watch, already knowing to expect a text message any second now.

_Beep beep, beep beep._

"Yup, right on time." Hiccup said to himself. He already knew what it would say. He read it anyways so that his phone wouldn't keep beeping with the reminder.

"_I have Gobber and the car tonight. Take the subway."_ That was it. No asking how he was, no see you tonight, nothing that may signify any type of friendliness. But Hiccup was used to that by now. This text message came every time Stoick said he was "working late", and that was pretty much every night. With a sigh he started his trek to the Bleeker Street subway station.

When he arrived, he walked down the stairs and into the station, wondering with a grimace what exactly that grey stuff hanging on the ceiling was. He paid his fare and immediately made his way down to the platform. Hiccup knew he could either take the 4 train or the 6 train to Grand Central Subway station at 42nd street to get back home to the condo on East 39th Street. The 6 train arrived first, and although it was the local, Hiccup decided to take it. He figured he would take it to 33rd Street station and just walk from there. He was in no rush to get home, and it was a nice evening, so why not? Little did he know just how much that decision would affect his life.

* * *

Hiccup exited the train at 33rd Street station, but came to the surface closer to East 32nd Street. He decided to take East 32nd east to 3rd Avenue, then up to East 39th Street; it was the same route he took almost every time he took the 6 train instead of the 4 train. He had only made it half a block before his "routine" was shattered. Voices were coming from the alley just ahead.

"I'm sorry, I don't have the money! But please, I just need some more time!" a panicked, male voice said.

Hiccup knew from just that line that something was off. This wasn't just some mugging, this was serious. As much as he wanted to run, this sounded like it may be the mob at work (I mean come on, that line practically screams stereotypical mob shakedown). So he just pushed himself up against the building and listened.

"You've had lots of time! This is the third time you are late this month! Something must be done." another voice said, clearly angry, but managing to stay surprisingly calm at the same time.

"I'll do anything! Please!"

"I'm afraid I have no choice."

"No, NO!"

The next thing Hiccup heard were two gun shots, a man's painful screaming, sobs, and footsteps coming his way.

"You're lucky you're not dead, next time have the money! And don't try to hide again; clearly I can find you."

Ok, so the man wasn't dead. That was good. But Hiccup would be if he didn't hide soon. If the shooter saw someone running down the street he would know that that person had overheard and possibly even seen the exchange, so that was out of the question, but there was nowhere nearby to hide. It didn't matter though, because before Hiccup could think anything else the man came out from the alley.

Hiccup couldn't stop himself from staring. The man was drop dead gorgeous. Black Armani suit; dark, long, straight hair; tanned skin that even in the dark light you could tell was what most people would call olive; and muscles you could see even beneath the suit. It was then that it struck Hiccup exactly who this was. He recognized him from pictures on his father's desk and down at the station. From the pictures in the newspaper articles he saw in class. He was looking at Toothless, a notorious member of the Fire Breathers gang. He couldn't believe how cool it was that he was so close to a member of the mob. Unfortunately, Hiccup didn't realize until it was too late that he had gasped, and Toothless looked right at him.

"_Oops_," was all Hiccup had time to think before Toothless had him pinned to the wall.

"What did you see?" Toothless demanded, a scowl evident on his face and an angry tone in his voice.

"N-nothing." Hiccup stuttered, his heart pounding and eyes wide. Technically it was the truth, he didn't SEE anything. But that wasn't where Hiccup's mind was, however. He was just trying not to lose his composure to fear, and trying especially hard not to focus on the gun in the hand Toothless wasn't using to keep him elevated and against the building.

"Seriously?"

"Yes."

Toothless was silent for a moment, so all Hiccup could hear was the other man from before crying in pain from the alley. Then, suddenly, the last thing Hiccup thought would happen happened. Toothless put him down.

"Alright. See you around." That was all Toothless said before he turned around, got into his car, and sped off. Hiccup would have sworn he saw a wink, but it was too dark to tell for sure.

Hiccup waited for the car to turn the corner before he continued along the road, in the same direction Toothless sped off. What? He couldn't help it if Toothless went in the same direction as his condo. His breathing was still heavy and his heart pounding, but he managed to walk in a straight line at least. And as he walked he only had two things on his mind: Toothless saying "see you around", and don't look down the alley. Hiccup knew he could probably help the poor man still crying out since he knew first aid, but if he helped the man Toothless may find out, and if he was serious with that "see you again" that may not be the best idea.

* * *

**A/N: Well hello again everyone! So I'll get straight to it. Two things. One, while I'm not sure if there are any examples in this chapter, I would like to say I do know how to spell. If you see a word spelled differently than you would normally see it, it may be because I am Canadian and some words are spelled differently in Canadian English when compared to American English, British English, or any other form of the English language. Second, judging by the response to the first chapter, there are a few people I believe that would like to see this story continued. However, I just want to double check that I didn't ruin it for all of them with this chapter XD. So, if you could be so kind as to tell me if you would still like to see this story continued in a review that would be great! (Sorry ADAMalchemist, your vote doesn't count XD)(And I promise my A/Ns will get shorter after this!)**


	3. Chapter 3

**A/N: Alright so since this chapter is here that means that people wanted to see this continued! So onwards and upwards! I do want to apologize though at how long this took. For those of you who don't know, in Canada (and some other countries) it is the Labour Day long weekend, so I spent a lot of time with family and didn't have much time to write/edit/post. So from now on I am going to post a deadline for myself at the bottom of each chapter for the next update. Let's just hope I don't forget that too XD.**

**I'd like to thank Warrior Nun, Heeeeeeey, suzuki bears, Guest, swade2, and Sinattea for their reviews. It's because of you guys (and girls) especially that this story is being continued. **

* * *

It was just past 7am when Hiccup rolled out of bed Friday morning. Fortunately his awful 12 hour day on Thursday meant he managed to get Fridays off, but he still let the sun wake him early like he did every morning. He never really wanted to sleep in, because he'd rather attempt to enjoy the day instead of just laying in bed.

When he was finally standing and started making his way to the bathroom, Hiccup made the unfortunate mistake of looking at the doorway he was walking towards rather than paying attention to where he was stepping. He accidentally stepped on some scattered papers on the floor and slid a few feet before landing flat on his butt.

'_Well today's off to a great start,'_ Hiccup thought to himself while rubbing his sore lower back. _'I wonder what else is going to go wrong today.'_

Hiccup carefully made the rest of the short trip to the bathroom, but not before making sure those pesky papers were moved off of the floor. When he arrived he turned on the shower, but brushed his teeth before getting in. He knew how long it takes the hot water sometimes. Unfortunately when he finally got into the shower the extra time hadn't made a difference; he may as well have been showering in an arctic snowstorm.

_'I guess that's what I get for opening my big fat brain earlier.'_ Hiccup made quick work of his cold shower before going back to his room, carefully watching where he stepped as he got into a red long sleeve t-shirt and the same pair of jeans as yesterday. Next stop, the kitchen.

When he arrived the first thing he noticed (and it would have been pretty hard not to notice) was the absence of his father. The daily newspaper was already neatly folded and in the recycling bin, indicating his father was already gone for the day. With the house to himself, Hiccup decided to make himself a big breakfast. Cooking was something you picked up pretty quickly when the main chef in the house was…no longer there and his father was constantly out.

It only took Hiccup 25 minutes to whip up a breakfast including a ham and cheese omelette with red onion and pepper, breakfast sausages, and fried potatoes. It made a lot of dishes, but Hiccup thought it was worth it. As he ate he considered what he would do that day. He didn't have any homework to do and with no job and no friends, his only real options were to read ahead in his textbooks or go out and walk around the city. He opted for the latter, but after he finished the dishes.

* * *

Unfortunately at 8:30 in the morning the two elevators were at their busiest point of the morning. Hiccup waited for two full elevators to pass before he just decided to take the stairs. He didn't have to get anywhere quickly and it was only going down so it wasn't that bad. In the end it only took him five minutes to go down the twenty seven flights of stairs.

Walking out into the streets of New York City, Hiccup was greeted by two things: a mildly overcast sky, and hoards of people. He didn't want to get caught out in the rain and considered just going back up to the apartment, but the thought of having to either wait for an elevator or climb all of those stairs changed his mind instantly. So instead he merged into the crowd and headed east on East 39th.

He made it to 3rd Avenue where he turned north, then went west on 42nd Street. When he was almost at Madison Avenue he glanced behind him, and noticed a black car with abnormally dark windows. Normally that wouldn't be anything Hiccup would take notice of, but the car was driving way too slowly considering there were no other cars in front of it. New Yorkers never drove slowly if they could help it, and the car had New York state plates. If Hiccup wouldn't have known any better, he would have said the car was following him. He would have thought that it was Gobber since it was a black Lincoln Continental, but the plates were wrong.

It was when he was approaching 5th Avenue that Hiccup started to become a little suspicious. This car never drove past him even though the road was (surprisingly) clear. Hiccup decided to turn down 5th Avenue just to see what the car would do. When he glanced back, the car had followed, still at a creeping pace.

_'Okay, this is officially weird,'_ Hiccup thought. _'I highly doubt my father is having someone follow me, so what's up with this car? Maybe I should call dad and ask if he has anything to do with it? No, he never answers my calls….'_

Hiccup decided to see if he could losing the car by going down 40th Street the opposite way of the traffic flow. But before he did, he made sure he had memorized the license plate on the car: "AJD4961".

As Hiccup walked west on 40th, he resisted the urge to look behind him to see of the car was still there until he was halfway down the block. The car was finally gone, and Hiccup breathed a sigh of relief. Apparently the car driver wasn't so crazy as to go the wrong way down a one way. He looked around and decided that since he was close to Times Square, he may as well go there and do some window shopping to pass the time.

* * *

It only took him 5 minutes to get to Times Square, and as always, it was packed with tourists. Hiccup walked around a few of the stores in the general vicinity for a little while before he sat down at one of the tables in the middle of the square just to people watch. It's amazing what you can see sometimes. He saw all of the people going into the stores and coming out with bags, and others going into the stores in their uniforms for their part time jobs. He really wished he could get a part time job and make some spending money of his own, but his father forbade it for reasons unknown to Hiccup and Hiccup didn't want to find out what his father would do in that scenario. Probably launch a whole investigation into the store and give them legal troubles until they fired him.

Rather than sit around and be jealous, Hiccup decided to continue his walk. It was getting close to 1pm, so thought he would find place to grab lunch. He may not have had a job for his money, but at least his allowance from his father was enough to have a little fun. Every week his father would deposit the sum of money directly into his bank account. It wasn't much, but it was something, and Hiccup always managed to save a little bit of it. He just wished he had more.

He decided on the McDonalds. The line was massive as it always was, but Hiccup waited patiently. He decided on a Big Mac combo, and managed to get a table looking out onto the street. He ate slowly, savouring each bite of greasy goodness. After all, if he ate quickly he'd have to leave sooner. At least the food gave him something to pass the time. He managed to pull off sitting there till 2pm until he noticed the manager looking in his direction, and he decided that it was best to leave.

* * *

Walking south on 7th Avenue out of Times Square, Hiccup was startled by a car horn. He really shouldn't have been, he lived in New York after all, but this one was really close. He turned around to see a car zooming past a car stopped in the curb lane. Or at least Hiccup thought it was stopped. As soon as Hiccup started walking again the car slowly started driving, never passing him.

_'Oh no way, not again,'_ Hiccup thought to himself while constantly glancing over his shoulder. _'Yup, AJD4961, it's the same car. Who the heck is this?'_

Hiccup stopped walking and looked directly at the car. The windows were tinted black almost like a limo, so Hiccup couldn't see inside. The car had come to a stop when Hiccup had (much to the disdain of the other cars behind it), but now that Hiccup was officially staring it, it started moving again and took a right onto West 39th, where it stopped just around the corner, a couple of car lengths in.

Hiccup knew he had two options: he could keep walking and try to lose the car again, or he could go up to it and find out why they were following him. While the second option was dangerous, something told Hiccup that if he chose the first option the car would continue following him until he chose option two.

Against his better judgement, Hiccup turned down West 39th and cautiously approached the car. As he was approaching, he heard the groan of the window as it was slowly rolled down a crack and observed that the street was deserted except for himself and the car.

"Hiccup?" a voice asked from inside.

Hiccup could tell it was a male voice, but that's all he knew. He didn't believe he had ever heard the voice before; it didn't sound familiar to him.

Before Hiccup even had the chance to respond, another voice (female this time) came from within and said, "Of course it's him, now would you hurry up?"

"Okay fine, you take the fun out of everything," the first voice replied.

Hiccup barely had time to register what was going on before the door flew open, someone jumped out, a bag was thrown over his head and he was pulled into the car. The person moved so fast he didn't even have time to scream before he heard the door slam shut and felt the car start to move.

* * *

Hiccup didn't know what to do. He was internally freaking out but trying to remain as cool as possible on the outside. He didn't know if he should fight or stay still, scream or remain quiet. One thing he didn't have a choice of is listening to the other two people in the car.

"Would you take that bag off his head?" the female voice said.

"Why? It's more fun this way."

"How is it more fun?"

"It's more like in the movies!"

"Well this isn't a movie! And it just looks stupid."

"Why are you always so against my fun?"

"Just take the bag off him before I come back there and beat you into doing it."

"You couldn't beat me if you tried."

"You want to test that theory right this second? I won't stop and we could crash into the walls of the tunnel."

"Cool, carnage!"

"You'll be unconscious before you get to see any of it."

"Ugh, fine."

The bag was removed and Hiccup was temporarily blinded by the change of lighting. When his vision cleared, Hiccup took the chance to look around. They had exited the tunnel and were driving through what appeared be to Queens in the all-black car. The car was being driven by a skinny girl with long blonde hair, while the guy in the back seat with Hiccup appeared to be her twin. The girl was watching the road, but the guy was looking straight at Hiccup.

"Um, hi?" was all Hiccup could get out.

"Hey, no talking!" the male barked.

"Oh shut up Tuffnut!" the girl in the front snapped. "Hey, I'm Ruffnut, and that, unfortunately, is my brother Tuffnut. He has a need to be weird as you saw with the bag earlier."

"Hey! Do not!" Tuffnut retorted.

They were about to get into another argument, but Hiccup managed to at least delay them this time.

"Um, excuse me, but could you tell me what you want with me?" Hiccup asked.

It was Ruffnut who supplied the answer. "Us? Nothing. It's…our employer who wants to see you. We're just the delivery girls," she said with a smile.

"Yeah, what she said. Wait, what?" Tuffnut's expression had gone from a smirk to confusion in under a second.

Ruffnut started cracking up, but instead of another threat Tuffnut just gave her an unimpressed look.

"And what about the no theatrics thing, huh? I'm pretty sure that answer qualifies as stereotypical theatrics."

"Well in this case it's acceptable," Ruffnut responded. "We don't know how our employer wants to deal with Hiccup here, so we don't want to ruin anything. Nothing could have been ruined by getting him in a less stupid way."

"Getting me? Don't you mean kidnapping me?" Hiccup asked. But his question fell on deaf ears as Ruffnut and Tuffnut had gotten into another one of their arguments.

Hiccup just decided to give up on asking the two questions; they clearly weren't going to tell him anything. Instead he decided to try and figure things out in his head. Questions such as "who is their employer" and "how far out of the city are they taking me" went through his head. Then he started wondering if he managed to get the door open and jump, could he survive? Or if he didn't, how long would it take his father to even notice he was missing? Would he even care? Not liking where the thought process was going and not liking his odds of jumping at this speed, Hiccup decided to just sit back and see what would happen, or at least wait until they got off the freeway.

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**Next Update: On or before September 8**

**And also, you see that box? The one just below this? It's hungry, and it feeds off of your reviews. Please don't let the poor innocent box starve...**


	4. Chapter 4

**Hello lovely people! So a combination of a not so stellar day at work and a few of my favourite stories updating today encouraged me to finish writing and editing this chapter early. So tada! One or two days ahead of schedule, depending on where you live on this planet.**

**Due to an unfortunate internet situation, my beta reader (ADAMalchemist) is out of commission, so I was the only one editing this chapter. I hope I didn't leave too many mistakes...but anyways, without internet I know he is sad and I don't like it when my friends are sad. And you know what would make him happy? Having lots of nice reviews of his amazing story "Philophobia" to receive when he gets his internet back! (This is my story I'm allowed to do a little advertising in it XD)**

**OK, I'm done with the rambling! (At least till the end of the chapter)**

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It was almost an hour later that they pulled into an industrial complex that felt like it was in the middle of nowhere. Hiccup had considered jumping out when they had gotten off the freeway and hit the side streets, but the doors were locked and if he tried to unlock one the male twin would probably figure out what he was trying to do and stop him, possibly with some unfortunate consequences. And quite frankly even if he managed to get the door open he couldn't honestly convince himself that he would have the courage to jump. Besides, even on the freeway he had decided that probably the best way to get out of this alive was to cooperate, at least until he was left alone and had a chance to escape discreetly. That was what his mother had told him to do if he was ever in a situation like this, and she had been a smart woman and cop.

Hiccup looked around as they drove through the complex, and his eyes were greeted with unmaintained streets riddled with potholes, broken road and street signs that were illegible after who knows how many months or even years of abuse by the weather, abandoned buildings with wooden boards covering doors and windows, and overgrown grass and shrubbery. Plus, as if to make his view of the run down area even more cliché, it was starting to rain. Not too hard, but Hiccup could hear the faint impact of raindrops on the car roof.

Eventually they finally turned into the parking lot of an abandoned looking warehouse building. It was clear that the building used to be grey, but the paint was faded and peeling. Most of the letters in the company name on the side of the building were gone, with only a T, O, and S remaining. All of the windows were boarded up, just like most other buildings in the complex. Hiccup had no idea what the inside would look like, but if he was going inside hopefully it would look better than the outside.

The car drove to the back of the building, to where the large loading docks were. There was one that had a permanently constructed ramp leading up to the garage door, just large enough for a car to drive up. The car had to be readjusted a few times before it lined up perfectly with the narrow ramp, but eventually they were slowly driving up the incline. When the door blocked them from going any further, Ruffnut stopped the car and honked the horn three times.

It felt like 5 minutes had passed before anything happened. Five awkward, silent moments in the car with the twins. They weren't even bickering anymore which kind of surprised Hiccup. But finally the door opened just high enough for someone to duck out and walk up to the car. With the narrow ramp they had to walk sideways and at one point it almost looked like he was about to fall. At least the drop would have only been a few feet.

"What do you want?" the man asked, clearly not impressed with having to be out in the rain. He was short and pudgy and wore overalls, but that was all Hiccup could tell because he stayed out of the headlights and the shadows covered his face.

"What do you think we want idiot? We have Hiccup with us, now would you hurry up and let us in?" Ruffnut responded, clearly not impressed with being kept waiting.

"Don't talk to me like that," the man snapped as he poked not just his head but half of his body through the front window and into the car to look in the back seat. However even at this angle the shadows still danced across the man's face and prevented Hiccup from obtaining an accurate description. "Are you sure that's actually him?"

Ruffnut looked into the back seat before she said, "Oops, looks like we got the Queen of England instead! Stupid us Tuff." As the guy turned to her, most likely to comment on her sarcasm, he was greeted by a powerful slap to the face. The sound made even Hiccup flinch. "Of course that's him you idiot! Just compare him to the picture! Now hurry up and let us in!"

The man, rubbing his sore cheek and without saying another word, went back under the garage door and opened it the rest of the way from the inside. They drove in and Hiccup's jaw almost hit the floor.

The inside looked like a mechanic's garage, but this wasn't some type of cheap garage. Hiccup wasn't a car person, but these were cars pretty much everyone knows. The first cars on either side were a Ferrari and a Bugatti. Apparently the only spot to park was at the back of the garage, so that just gave Hiccup more opportunity to ogle some of the other cars. Mercedes, BMW, Jaguar, Land Rover, Bently, all the luxury car brands seemed to be there. There was even a Tesla.

Eventually they pulled into a spot at the back of the garage and both Ruffnut and Tuffnut got out after Ruffnut had unlocked the doors. Hiccup, deciding it would probably be best to get out as well, started reaching for his door only to have it pulled open by Tuffnut.

"Alright, let's hurry this up. As cool as this place is I want to get out of here sooner rather than later," he said.

Unfortunately Hiccup's time to ogle the cars was done, as the door into the other part of the building was right next to where Ruffnut had parked the car. Hiccup was lead through the doorway, up a flight of well-maintained dark wood stairs, and down the hall with the twins on either side of him.

Hiccup had to admit, with the way the inside of the building looked he would not have thought it was the same building that he had seen outside. Granted the garage area had cracked concrete floors, high ceilings with the steel beams exposed, and unpainted walls, but now they were walking down grand hallway with what appeared to be grey granite floors with black specks that sparkled and reflected the light from the chandeliers above, really nice art on the deep red walls, and a ceiling height that Hiccup estimated to be about 10 feet. Hiccup would almost think he had stepped into a luxury New York penthouse, not the other side of a beaten up warehouse.

Hiccup couldn't stop himself from looking around. The interior was too gorgeous to not stare at. Hiccup must have been conspicuous because Ruffnut took notice of his gawking.

"Yeah, definitely nice in here. He definitely put more work and money into his building than anyone else did theirs. And he's got good taste to boot. I wish I worked for him." Ruffnut seemed to be admiring the décor too, her eyes drifting between the paintings.

Hiccup took her possible distraction as an opportunity to try and divulge some information.

"So who do you work for? And who exactly is it that has good taste?" Hiccup tried to ask as calmly and nonchalantly as possible.

"We work, hey! Knock that off. We told you we can't tell you anything," Ruffnut said as she kept walking. Apparently Hiccup had taken a route that was a little too direct. He also had to wonder why Tuffnut was staying quiet this whole time.

They passed several doors along the hallway, all of which were closed and unlabelled. Hiccup let his mind wander, wondering just what was behind each closed door. What secrets lay behind each? What mysteries lay beyond the closed piece of wood? Hiccup didn't have much time to ponder before the twins came to a stop.

"Alright, here we are," Tuffnut stated.

"Are you sure it's this one?" Ruffnut asked.

"Uh, yeah, I think I can remember which door it is."

While the twins started another one of their arguments, Hiccup realized Ruffnut had a good point. The door they had stopped in front of looked exactly like all of the others. Brown, brass handle, wood, and a basic design where four rectangles were sunk into the wood. It wasn't even at the end of the hallway; it was right in the middle.

Deciding that the twins weren't going to stop arguing any time soon, Hiccup opened the door himself. When he walked in, he realized he was in an office. But this wasn't just any office; it was gorgeous. The room felt like it was almost the size of the entire apartment Hiccup lived in. It was a perfect square with something different on each wall, and a desk with three chairs in the middle. The desk was solid wood and beautifully carved with several different designs. There was nothing on the desk; no papers, no pens, no computer, nothing. The chair behind the desk was large and black leather, standing on wheels. The last two chairs, the ones on the close side of the desk, were large, comfy looking beige cloth armchairs. The walls were painted the same deep red as the hallway outside. The wall on his left had a massive gas fireplace, surrounded by intricate stone work and an open door just to the left of the fireplace revealing a bathroom. The wall with the door to the hallway on it housed several more gorgeous paintings. The wall on the right was a library, housing books on all topics, fiction and non-fiction. On second glance, however, Hiccup noticed that not a single book had its spine cracked. Finally, the last wall at the back was one large window, overlooking the garage that they had come into.

_'Great,'_ Hiccup thought to himself, _'no windows, no way out, so I guess I'm stuck here. Though I guess I was stuck here anyways. Where would I go if I got out? I'm in the middle of nowhere. They'd probably get to me before I could get to help.'_

Realizing there was no likely way of escape, Hiccup decided to just wait this whole thing out in the office. He could still hear the twins outside guarding the door, but he started looking over the books on the shelf. There really was everything. Hiccup saw everything from "War and Peace" to a book on public transit to a biography of Oprah Winfrey. After skimming the books, he went over to the window ogle the cars some more.

In the middle of looking at the cars, he suddenly noticed that the twins had stopped arguing, and another voice had joined them. Male, deep, and slightly familiar, but Hiccup couldn't quite place the voice.

"You're sure it's him?" the new voice asked.

"Well, he looks exactly like the picture and we found him in the area you said we would, so I'd assume."

"Okay, well I saw him going into the building last night after I met him…"

That was all Hiccup heard before his mind started to race again.

_'Last night? Who did I meet last night? Who could have seen me going into my building? I mean last night I,' _Hiccup stopped dead in his thoughts, eyes widening when it hit him. _'Toothless.'_

It was then that Hiccup's mind started to reel, and his feet started to pace.

_'That voice that was so familiar, it's Toothless. But what would he want to see me for? It must be about last night again. Does he think I told someone? Or worse, did he find out who my father is?' _That last thought stopped Hiccup dead in his tracks and drained most of the colour from Hiccup's face. What if he thought he had gone to his father about the events he "witnessed" last night? That could only end badly.

Hiccup's thoughts were interrupted by the clicking of the door handle and the creaking of the hinges. To hide his face, he kept staring out the window. He didn't know what it would accomplish, but he seemed to want to do anything to not look at Toothless, even though he knew it wouldn't last.

The footsteps approached slowly, but they never seemed unsure. They continued until they were right beside him.

"Beautiful, aren't they? Took me years to collect them all. Although to be honest I don't think I've ever driven half of them." Yup, the voice was definitely Toothless. Hiccup knew he couldn't delay it any longer, especially with Toothless standing so close. He glanced over, only to find Toothless already looking at him. He was wearing the exact same type of suit as yesterday, the only difference was the colour of his shirt. The smile on his face was the exact opposite of the deep fear that Hiccup was trying to supress, seemingly showing a sense of genuine happiness to see the boy again.

"Hello Hiccup."

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**DUN DUN DUN! I wonder how many people just screamed at me XD. I'm sorry, but I love a good cliffhanger.**

**Next Chapter: On or before September 14**

**Do you read this story faithfully?Are you happy I updated?  
Do you breathe oxygen?  
If you answered yes to any of these questions, it may be beneficial to your health to review!**


	5. Chapter 5

**Hello lovely people! I have returned! With a chapter no less! And I only have one thing to say before I get to the chapter. As you may have noticed, the cover picture of this story is my not so gorgeous face. That is because this story has no cover image of its own. That being said, if anyone reading this is even mildly artistic and feels inspired to make a cover pic for this story, I would be more than happy to use it. I'm not exactly expecting the responses to come flooding in (heck I'm not expecting any), but if you are interested, PM me or mention it in your review :)**

* * *

"Come, sit. I was hoping we could talk for a bit." Toothless gestured to the desk and chairs as he made his way to them.

Hiccup tried not to shake as he walked towards the armchairs on the far side of the desk. As he walked two pleas went through his head: "please don't let him kill me" and "please don't let him know who my father is". By the time he had gotten to the beige armchair Toothless was already sitting in the large leather chair, hands folded and resting casually on the desk, and a confident smirk on his face.

"Don't look so nervous, it's not like I'm going hurt you," Toothless chuckled, but it did little to put Hiccup at ease. Hiccup had several questions buzzing through his mind, but he decided it would be best to start at the beginning.

"How did you find out my name and where I live?"

Toothless took a moment to ponder the question, and Hiccup hoped that he hadn't angered the mobster by being too forward. In retrospect he should have let Toothless speak first. Plus that would have given him time to try and read Toothless' mood a little better. Hiccup still hadn't figured out his agenda yet.

"After I left, I circled around the block. I drove at a distance behind you until you entered a building, which I'm assuming is the building you live in. After you went in I asked the doorman and the security guard if they happened to know your name. It's amazing how freely people will give out information sometimes really."

"Okay, I guess that makes sense, but how on earth did you get my picture?"

Toothless chuckled before answering that one. "Actually, that one was a little harder. I had to hack into some of the security cams in the area and find you on the cameras. It took my best hacker 2 hours. But he did a good job of it; the picture of you is very good quality."

Hiccup didn't know what it was, but Toothless seemed a lot less intimidating when he was chuckling, or even just smiling. He seemed like a normal person. His smile just lit up his face.

"But enough of that, you're probably wondering why I had you brought here."

"It may have crossed my mind." Hiccup's breath hitched after he said that. Maybe using his trademark sarcasm with a man as powerful as Toothless wasn't the best idea. He had no idea if the man even had a sense of humour underneath his rock hard façade. Toothless either didn't care or didn't seem to notice.

"The truth is," Toothless said while standing up, and at the movement Hiccup visibly tensed, "I wanted to apologize for last night. I know you were just in the wrong spot at the wrong time. I just acted out of force of habit. Self-protective instincts if you will."

Hiccup wasn't sure how to respond to that. A violent mob member was apologizing? Has that EVER happened before? So Hiccup gave the only response he could think of, even if it did come out sounding like a question.

"It's okay?"

Toothless continued on like Hiccup had never said a word, pacing slowly around the office.

"I mean how old are you? Nineteen? Twenty?"

"I'm, uh, nineteen, but I'll be twenty next month." _'And now I sound like a child….'_

"And do you go to school?"

"Uh yeah, I go to NYU."

"Down in lower Manhattan, right?"

"Yeah."

"What are you studying?"

"I'm a first year in the architecture program."

"So you want to be an architect then?"

"Not really. The truth is I was kind of forced into it by my father. He only let me choose from a limited number of programs. I guess I figured that it was the least of all evils." It took a second before Hiccup thought to himself, _'Crap! Why would I mention my father? That just begs him to bring that into the conversation.'_ Fortunately Toothless didn't take the conversation in that direction.

"Well at least it's an interesting subject. Surely there must be something you like about it?"

_'Hiccup Haddock don't you dare let your mind wander to Jason right now.' _"Uh, I guess that it lets me be creative."

"Architecture is actually something I would have liked to study in university if I had had the chance to go. Well I guess I still could at one point, I mean I'm only twenty two, I've still got lots of time." It was here that Hiccup suddenly became interested in the conversation and started to feel a little more at ease.

"You're only twenty two?" He was barely older than Hiccup. For some reason that made him seem a little less scary. In another universe they may have actually been friends.

Once again, Toothless chuckled. "Yeah, you thought I was older?"

"Well you are quite," Hiccup started before he stopped himself. He had to be careful how he worded this. Well, there went the sense of ease. "Successful."

"Well I got my start at a young age. I don't really like to talk about it though."

_'Oh great,' _Hiccup thought to himself, _'I've gone and hit a sensitive topic, probably made him mad. Way to go.'_

Just then, Toothless' cell phone started to ring. As he checked the caller ID, he turned to Hiccup and said, "I'm sorry, I have to take this. I really do apologize for having to cut our meeting short. Ruff and Tuff are waiting outside the door still and they will take you home. Barf and Belch still owe me one more favour. It was nice to see you. Oh, and if you could do me a favour, please try to keep this place a secret. I'd rather not have too many people know about it."

"Uh, yeah, sure, no problem," was all Hiccup could say before Toothless picked up the phone, but he did manage to give Hiccup a wink.

Hiccup showed himself out of the office, closing the door with a soft click behind him. He found Ruffnut waiting solo outside of the door.

"So he let you live huh?" Ruffnut asked, and Hiccup wasn't sure if she was joking around or not. "Whatever. Tuffnut got called out, so I'm driving you home myself. Let's hurry up and get this done."

The walk back to the car seemed longer than the walk to the office from the car. It was as if time itself had slowed to a snail's pace. Maybe it was because it was the same scenery as the way in. It also didn't help that Ruffnut was walking several paces in front of him most of the way.

The walk down the monotonous (yet still quite lavish) hallway ended with the same stairs and the same car waiting at the bottom to take Hiccup home. Hiccup wondered how Tuffnut had left if the car he had gotten there in was still here, but Hiccup figured it best not to ask too many questions. He may not like the answer. Maybe not for that question per se, but you never know where a conversation may lead.

The garage door was already open, so Ruffnut just drove out and started back towards Manhattan. It was a full 10 minutes before a single word was exchanged to break the deafening silence.

"Sorry about my brother earlier today, I'm not sure why he insists on doing everything in such a ridiculous manner."

Hiccup almost fell out of his seat. The first words said on the trip back, and it was an apology? The second one that day from someone in the mob? And from Ruffnut? She did not strike Hiccup as the type that would give an apology for anything, let alone her brother. They were constantly bickering.

Hiccup's confusion was quickly ended when Ruffnut added, "but don't expect any more apologies from me. I'm not the apologetic type."

The awkward silence returned for a few moments, and while Hiccup said to himself he didn't want to ask any questions, his curiosity was starting to get to him.

"So, who are Barf and Belch?"

"Hm? Oh, Barf and Belch are Tuffnut and my employers."

"Wait, you mean you don't work for Toothless?"

"No, hardly anyone works for Toothless. The only people that do work for him have nothing to do with his mob work directly though. You know, just a couple of people behind the scenes. Like the mechanic. We're doing this for him because Barf and Belch owe him a favour."

"Why did they owe Toothless a favour?"

"Do you really want to know?"

It was then that Hiccup remembered the whole reasoning behind not wanting to ask questions. Some things really are better left unknown, and thankfully Ruffnut reminded him of that before it went too far.

"No, actually. I just don't understand how this all works I guess."

"Well it's quite simple."

Hiccup's statement was rhetorical, but apparently Ruffnut didn't catch on. And Hiccup figured it was probably best not to interrupt someone who could easily beat you to a pulp without breaking a sweat.

"Basically, the Fire Breathers gang is broken into 5 groups. Toothless leads one group, Barf and Belch another, et cetera, et cetera. And all five of those groups are controlled by the leader of the gang, who goes by the name of Red Death, or RD for short. Sometimes the leaders do each other favours, you know, certain tasks or jobs, and eventually those favours get called in. By driving you from and to Manhattan I am paying back a favour Barf and Belch owed Toothless."

Hiccup just nodded and mumbled affirmatively. He did not want to know what Toothless had done to earn the favour. In his best interest, he decided to deal with the silence the rest of the way to Manhattan.

* * *

They emerged from the Queens Midtown Tunnel onto Tunnel Exit Street, where they got stuck in the stereotypical bumper to bumper New York traffic. It took a whole 10 minutes to get from the tunnel to East 39th Street. Hiccup realized afterwards he probably could have walked it faster. It only took a few seconds after taking the turn onto 39th before Ruffnut stopped right outside Hiccup's building. He wasn't sure he liked the fact that she knew where he lived, but there wasn't much he could do about that.

Hiccup glanced out the windows, making sure no one who could recognize him would see him getting out of the car, before he gave Ruffnut a quick, "thanks," and jumped out, slamming the door behind him. The car didn't necessarily have any clues that it would be a mob car, but better safe than sorry. Then it hit him that that would be another reason he should have walked from Tunnel Exit Street.

As Hiccup slowly ascended in the elevator, he let his mind wander back to his conversation with Toothless. He didn't realize until now just how much personal information he had given to Toothless. Toothless, either from finding out directly from him or not, knew his address, name, age, where he went to school, what he was studying, why he was studying it, and about his not so great relationship with his father. All the basics, plus a little more. Why did that information all slip out so easily? It almost seemed like Toothless was trying to get to know him, like someone does when making a new friend.

The elevator dinged softly as it reached Hiccup's floor, but while the elevator had stopped, Hiccup's thoughts were still moving rapidly. Why would Toothless want to be his friend? Is that even what was going on? If it was, would Hiccup want someone like Toothless as a friend? What if his dad found out? What would he do to him or Toothless? Toothless winked at the end of their meeting today, and possibly when they first met, maybe Toothless wanted to be more than friends?

Hiccup stopped himself there. While he did find Toothless attractive, there was no way Toothless rolled like that, was there? He decided to stop thinking about it instantly. He was tired, so his brain was probably not functioning properly.

He fumbled with his keys and eventually managed to unlock the door.

"Hello?" he called, not really expecting a response and not being surprised when there wasn't one.

Hiccup glanced at the clock, then was forced to do a double take. 9:30pm. Clearly his father was "working late", but that wasn't what had shocked him. Either traffic was a lot worse on the way back then he thought or the time at the warehouse took longer than he thought. He had missed dinner, but with all of the excitement he wasn't even hungry. It may have still been relatively early, but that didn't stop Hiccup as he stumbled to his room, kicked off his jeans, and he was out before his head even hit the pillow. Hopefully tomorrow would be a little less exhausting.

* * *

**No cliffhanger this time...oh well  
**

**Next chapter: On or before September 21**

**Poor Hiccup is exhausted :( But you know what gives him energy? Your reviews! So help Hiccup get his energy back, because something tells me he is going to need it...**


	6. Chapter 6

**Has it been a week already? Wow. But here is the next chapter, as promised :)**

**And I would like to take this opportunity to thank the amazing, spectacular, wonderful Warrior Nun for volunteering to make the cover image for this story! It'll go up once it's ready.  
**

**OK, story time!**

* * *

Not only did Hiccup go to bed uncharacteristically early, but he slept unusually late as well. It was almost 11am when Hiccup finally rolled out of bed. Immediately after getting up, his stomach grumbled quite painfully and it almost knocked Hiccup over. Hiccup figured that's what he got for skipping dinner the night before. He started walking to the kitchen without even bothering to throw on new clothes.

That was a bad choice, because when he got to the kitchen he almost fell over for the second time that day. Inconceivably, Stoick was home. It may have been Saturday, but Stoick always worked Saturdays. And on top of all of this, Stoick wasn't reading the paper or watching TV, he was just sitting there, as if waiting for Hiccup.

"Morning son. How'd you sleep?"

Ok, Hiccup had to think this through. Stoick was home, in the middle of the day, not doing anything, and was actually taking if interest in his son? The first thing that went through Hiccup's mind was, _'who are you and what have you done with Stoick?'_ Hiccup decided on the diplomatic approach over the confrontational one however.

"Uh, fine, thanks. How about you?"

"Fine."

For some reason, Hiccup's stomach decided that now would be the ideal time to give a less painful but much louder rumble than last time. Both Stoick and he glanced down to his stomach, with Stoick raising an eyebrow.

"Well, sounds like someone's hungry! Why don't you throw on some proper clothes and we'll go out for lunch, hm?"

Wait, now his father was inviting him to go out for lunch? Something was wrong. Was he failing a course? Did he do something that would put him in legal trouble? Hiccup couldn't think of anything, and he was fairly certain his father knew nothing about his "meeting" yesterday, so he did the only thing he really could in this situation: he turned around, went to his room, and got changed.

* * *

When father and son had finally made their way downstairs, Gobber was waiting for them in the car. Hiccup got into the back seat and crawled over to the other side while his father climbed in behind him.

"Katz's Deli, right Stoick?" Gobber asked from the front seat while glancing in the rear view.

"Yes Gobber, thank you."

As Gobber started to pull away, Hiccup only had one thing on his mind and he figured it was better to get it out of the way sooner rather than later.

"Dad, did I uh, did I do something wrong?" Hiccup clenched his eyes shut and waited for the possibly impending explosion from his father. The last thing he expected was a chuckle, but that's what he got. In retrospect, when was the last time he had heard his father come even remotely close to laughing? He couldn't recall.

"No son, unless there's something I don't know. There isn't anything I don't know, is there?"

"No, of course not," Hiccup replied, possibly a little too quickly. If he did his father didn't seem to notice. But there was a complete lie. He had witnessed a crime, been brought to a wanted man's hangout, and hadn't reported any of this. But Hiccup couldn't bring himself to do that to Toothless. Other than the kidnapping, which had been a little terrifying at first, Toothless had given him no reason to want to say anything. And also, that kidnapping was just to apologize.

"Alright then," was all he got as a reply. At least that confirmed Hiccup's hope that his father was still in the dark about his recent events.

Then came the awkward silence. What was it with Hiccup and awkward silences in cars recently? He looked into the rear-view from the back and hoped to catch Gobber's eyes with his 'help me' look. Fortunately Gobber was there for him.

"So, Stoick, I was actually hoping to ask…"

That was all Hiccup heard before he zoned out. Thank goodness for Gobber. It was almost as if Gobber could sense when he needed help. Hiccup wasn't sure he could have lasted the whole car ride with the awkward silence that might have occurred.

After a few minutes, they were still talking, and Hiccup had a feeling Gobber could keep the conversation going all the way to the deli, not that he minded. But it did give Hiccup's mind some time to wander once more. Why did Stoick suddenly want to have lunch with him? If he wasn't his trouble, and it definitely wasn't anyone's birthday, what could this possibly be about? Then it hit him.

* * *

It was only ten more minutes before Gobber pulled up in front of the small brick building on East Houston Street labelled Katz's Deli. Something told Hiccup this would be his best chance to test his theory, so he took advantage of the situation.

"Dad, you go in and get a table. My cell phone fell out of my pocket, so I'm just going to find it and then I'll come in."

"Alright, but be quick."

The moment the door was closed Hiccup turned to Gobber.

"Alright, what are you up to?" Hiccup demanded. "My father hasn't wanted to be friendly with me since before I told him I was gay. This has you written all over it."

"I assure you I have no idea what you're talking about."

"You're a terrible liar, you know that?"

"Alright fine! The other day I had a conversation with Stoick. I told him that he needs to let you get out there more and give you some more freedoms. All the rules he has on you aren't healthy. I told him that if he actually took an interest in you more and tried to get to know you he'd realize that it would be ok to loosen the leash. So to speak."

Hiccup couldn't help but smile. "Wow, Gobber, thank you. That means a lot to me that you would do that for me." And Hiccup really did feel grateful. It was nice to know someone was out there looking out for him. "But do you really think that this could work? I mean I don't think a lunch is enough to change his views of me."

"You won't know if you don't try Hiccup."

Well, there was no arguing with that logic. Maybe things would finally work out for him. Maybe he could have a normal relationship with his father. Maybe he could have a normal life. This lunch could be the best thing that ever happened for him, right?

* * *

Wrong. There wasn't even enough time for anything to go right. The minute Hiccup walked inside, his father was just about to get shown to a table. As they went to the table they got, Hiccup's heart stopped. There were 2 tables side by side, and they were going to the one on the left. At the left side of the table on the right were two guys in odd green suits, and they looked so similar Hiccup would have assumed they were twins. On the right side of the table, looking directly at the table that he would soon be sitting at, was none other than Toothless.

Hiccup panicked. Toothless was going to see him here with his father, he would realize who he was, and who knows how mad he would be? And what would happen if his father saw Toothless? If Hiccup let that happen Toothless might blame him. This could be very bad. Hiccup decided he needed to act, but he couldn't just ask to leave, that would arise too much suspicion. He needed to act fast as his father was headed straight for the seat that would look straight at Toothless.

"Uh, dad, I'm actually a little chilly, can I sit on the left side? There's more sun light shining on that seat." Yeah, real brilliant.

"Uh, sure." Stoick said before heading for the other seat. Hiccup held his breath, but fortunately it seemed that Toothless hadn't seen Stoick or himself, nor had Stoick seen Toothless. That didn't stop Hiccup from being on edge though. He kept glancing over to Toothless every fifteen seconds or so, cursing himself every time he did so and silently hoping no one noticed.

He didn't have to worry about being distracted from his twitch by conversation, because his conversation with Stoick wore out within two minutes. The only thing Stoick ever did was work and go out, and both of those topics were off limits for their differing reasons. On the other side, Stoick had little interest in architecture other than being willing to say it was a respectable profession, and other than that Hiccup had no life or real interests to talk about because he had no life to speak of or it was a topic Hiccup had a feeling Stoick was fundamentally opposed to. That pretty much secured the failure of the lunch within the first few minutes.

As Stoick continued to focus solely on the menu, Hiccup kept glancing to Toothless, hoping he wouldn't notice him in return. Lunch may be disaster number one, but Hiccup was determined to avoid disaster number two.

Not a few seconds later did the waitress arrive and start to take their orders. She got through Stoick's order no problem, a roast beef sandwich, but as soon as the first syllable of Hiccup's chicken club order left his mouth, Toothless' head snapped up so fast he was surprised it didn't hurt his neck. Hiccup had been strategically timing what little talking he had been doing so he was talking at the same time as Toothless, hoping that Toothless would be too distracted to notice anyone else's voice over his own. However, when he started to order, he hadn't realized Toothless had stopped talking.

Hiccup faltered, but to avoid suspicion he finished his order and smiled at the waitress. It was a good thing he wasn't talking to his father right now, because his mind probably wouldn't have allowed him to form a coherent thought. Disaster number two had just occurred. This was officially the worst day of Hiccup's life.

Toothless stood and started to walk towards the table, a smile on his face like he was actually happy to see Hiccup. That lasted all of three seconds before Toothless realized who he was sitting with. It was a good thing he did notice or that could have become even more awkward. Toothless' smile instantly fell as his eyes widened. He mouthed something like "we'll talk later" and performed a quick about face. He immediately waved the waitress over and although Hiccup couldn't hear him, he was pretty sure he said something along the lines of 'check please!'

Toothless didn't even sit down. He stood until the waitress came back with the bill, whispered something to the other men, paid the bill, and then all three quickly exited the building.

Hiccup couldn't stop the possibilities of the consequences from spinning through his mind.

"Hiccup? Hiccup! What on earth are you looking at?" Stoick asked as he spun around to look at the table Toothless had just been occupying.

That snapped Hiccup out of his daze.

"Oh, nothing, sorry." Hiccup immediately turned his attention to the sandwich that was placed in front of him. Those were the last words that would be exchanged during the lunch.

* * *

As they finished up, Hiccup noticed Gobber pulling up outside, so he told his father he'd go tell Gobber they were coming while he paid.

Hiccup got into the car and closed the door behind himself. Gobber didn't even have a chance to get a word in before Hiccup started talking.

"Gods Gobber, that was just terrible. This may be the worst day of my life."

"What? Why? What happened?" Gobber asked, genuinely concerned with a frown creasing his face.

"Well first of all, we barely spoke at all. I think a total of three full sentences were exchanged. We spoke more this morning before this whole ordeal. Then, T…this guy who I think wants to be my friend was in there, and he almost came up to the table. There's no telling how dad would have reacted! It's a good think he had the sense to stay away. This was just awful," Hiccup moaned, burying his face in his palms.

"Oh," Gobber said sadly, eyes downcast, "I'm sorry. I shouldn't have interfered. This is all my fault."

"What? No no no no, don't even think that Gobber! You made an effort to try and make my life a little better. Maybe it didn't work, but you tried, and for that I thank you. You know, sometimes I wish you were my father instead."

Hiccup cut himself off there as his father opened the car door to climb in himself. He didn't even say anything before Gobber took off to head up 1st Avenue. This time there was no awkward silence though as Gobber knew to start a conversation right away to keep Stoick away from the topic of the lunch. That was another great thing about Gobber, he always knew how to mediate the awkward father-son relationship that existed between Hiccup and Stoick.

With Hiccup's mind off of one disaster, that allowed the other to pop back up. What was Toothless going to think? Obviously now he knew that Hiccup was the son or at least close to the head detective on his case. Something told Hiccup that news would not be handled well.

Fortunately, even with the Saturday traffic, the car ride home was quick. Hiccup wanted nothing more than to go up to the condo, lock himself in his room, and not come out for at least the rest of the day. Hopefully that would give him enough time to think everything through a little better before he'd have to deal with it all.

* * *

**Next chapter: On or before September 29**

**Ugh, Hiccup's life sucks right now with the predicament he is in. Why not cheer him up with a review?**


	7. Chapter 7

**Hey everyone! So this chapter was finished up just today (school, OTL) so I wasn't sure if ADAMalchemist would have enough time to beta is and get it back to me to get in before the deadline. As such, I apologize for any horrendous mistakes that my own proof reading didn't catch. Enjoy!**

* * *

Hiccup woke up Sunday morning, but immediately wished he could go back to sleep. Yesterday had been a disaster, and he did not want to deal with any of the possible consequences, repercussions, or anything else even remotely along those lines. He was pretty sure that Toothless would want to see him again after that, heck he knew for sure because he had mouthed it to him, and he also knew he wouldn't take no for an answer. Hiccup didn't think that Toothless would cause him any harm, but then again, he barely knew the guy. No, Toothless was too nice a guy and Hiccup hadn't done anything wrong. Right? Great, now he kind of wanted to see Toothless to prove his innocence.

After looking at the neon green glow of his alarm clock and reading 9:30, Hiccup tried to close his eyes and return to a state of blissful slumber, but his body would have none of that. No matter what he tried he only became more and more awake as time passed.

Hiccup finally caved to his body's demand to get out of bed, but that didn't mean he had to go through his morning routine very quickly. He actually made his bed today, making sure it was so well made he could bounce a quarter off of it, before proceeding to the bathroom. He made sure to watch the floor as he walked, and this time he managed to avoid slipping on the papers (how had they ended up back on the floor?).

As usual, Hiccup turned on the shower before brushing his teeth to allow the water to (hopefully) heat up. He applied the minty toothpaste to his toothbrush and slowly started brushing. Here Hiccup wasn't actually sure if his slow movements were to give the water more time to heat up or to delay him from having to face his day even longer.

Regardless, Hiccup finished brushing his teeth, stripped off his pajamas, and got into the shower, hoping for some hot water today. He did see some steam, so that was promising.

"Gah! Son of a," Hiccup started before vocalizing quite possibly every cuss he had ever heard, and most likely inventing a few new ones in the process. Hiccup could never understand how some days the water would be ice cold, but other days on the same setting the water would feel like lava from a volcano. At least he could make hot water more bearable by turning it down; not something he could do when the water was only cold. Subconsciously he chalked that up as a win for the morning.

Taking full advantage of the now warm water (and still wanting to prevent himself from having to face his day), Hiccup gave himself what was probably the most thorough shower of his life. It took him a good fourty five minutes, and he scrubbed every part of his body at least twice (including his hair).

The next excessively drawn out task Hiccup performed was breakfast. Since Hiccup had slept in a little by his standards, his father was already gone, with the newspaper in the recycle. And that was just the way Hiccup liked it. It was just easier when he wasn't there. Today Hiccup decided on a menu of pancakes and eggs.

* * *

By 1 o'clock in the afternoon Hiccup had run out of stuff to do. He had gone through his entire morning routine, had breakfast, cleaned up the dishes from said breakfast, and even vacuumed and dusted the condo. Now all he was doing was sitting lazily on the couch watching some random documentary on some near extinct animal. It was too boring for even Hiccup to pay attention.

Hiccup flicked off the television and swung himself off the couch. Glancing through the window and down at the street he noticed that it wasn't horrendously packed, and looking up at the sky he saw the weather was clear.

It was then that Hiccup reasoned that couldn't stay inside for the rest of his life, and that if he dealt with the Toothless issue sooner rather than later it would probably be for the better. Grabbing his zip up sweater just in case, Hiccup walked out of the condo door and walked towards the elevator.

* * *

Hiccup may have been going down in the elevator, but his pulse was going way up. He took deep, heavy breaths, and fortunately he was alone in the elevator or that could have been awkward. He was so wound up when the elevator dinged on the ground floor he gave a startled shriek. At least no one in the lobby let on that they'd heard.

As Hiccup walked out the front doors, he figured he would make it about three blocks before Toothless' car would be following right behind him. Just as he started walking, however, a car horn blasted, scaring him just as it had two days ago. When he turned around to look, he saw a slow moving Lincoln Continental holding up traffic. The licence plate was "AJD4961".

Hiccup couldn't help but be amazed. _'Three blocks. I didn't even make it three steps! Well, better get this over with.'_

Hiccup walked right up to the car and yanked the door open, faking a sense of bravery, expecting to see Tuffnut sitting in the back seat again. He was slightly surprised that the back seat was empty.

"If you're going to get in, would you hurry up and do it? This guy's honking is giving me a headache." The voice was female, but it definitely wasn't Ruffnut. He hesitated, but then remembered that either way this was Toothless' car, so he'd end up at the same destination. Now all he could do was hope that his belief that Toothless wouldn't want to hurt him was right.

He climbed in and immediately after he shut the door, the driver gunned it. After Hiccup recovered from the lurch, he took the time to look at his new driver. She was blonde like Ruffnut, but she kept her hair in a braid. She was just as skinny too.

"Well, that was easy. Ruff and Tuff made it sound like it was so hard to get you." The girl said, eyes unmoving from the road.

Hiccup started a conversation before he could catch himself.

"Well in their defence at the time I didn't know who they were or what they wanted. Although the bag may have complicated things a little."

"Ugh, Tuffnut used the stupid bag thing again? It's so stupid. I don't know why he does that." Hiccup could tell that the exasperation in her voice was genuine. It made him wonder just how many other people Tuffnut had done that to, and just what their….fates….had been.

_'Bad thought process, Hiccup. Back it up.'_

"So, what's your name?"

"Astrid."

"You work for Toothless?"

"No."

"Barf and Belch?"

"No."

"So who do you work for?"

When Astrid spoke next, it wasn't an answer to the question. It was accompanied by a blast of the car horn and a call of, "out of the way, moron!"

Astrid never got around to answering Hiccup's question, and with her angered mumbling after the outburst, Hiccup figured it would be for the best not to interrupt. The car ride the rest of the way was silent, but at least Astrid had the music on. He hadn't noticed it before, but now that there was nothing else to focus on, he could hear Imagine Dragons coming from the speakers. He sit back, enjoyed the music, and waited to arrive back at the seemingly run down warehouse.

* * *

Hiccup saw all the same scenery on the way in this time as he did last time, except this time it wasn't raining. Even in the different light though he was able to pick out the building from down the street. Astrid drove around the back of the building, and the only difference from last time was that this time the door to the garage was already open. Hiccup thought that if he had a car collection like Toothless had he would definitely make sure that the door was closed at ALL times.

Astrid parked the car in the same spot at the back of the garage, and Hiccup got out right away this time. As he was getting out, though, he started to look around for the window that would show Toothless' office. He still vividly remembered the view from it from last time. Eventually he found it on the far wall. What he also found was Toothless standing just inside the window, hands folded behind him, and watching Hiccup with an unreadable expression. Maybe coming willingly hadn't been the best idea. Too late now. Better get this over with.

* * *

Hiccup didn't know what to feel when walking down the hallway. All the doors were once again closed, so he couldn't look into the rooms to take his mind temporarily off of what lie ahead. The walk to the office door seemed shorter this time, and when they arrived, Astrid just nodded towards the door and walked off.

Hiccup waited until she was down the hall before he started to reach for the door handle. Just before he grabbed it, he stopped himself. What was the etiquette in a situation like this? Toothless knew he was coming, but it was a closed door, so he should knock, right? After arguing with himself for a few seconds, Hiccup settled on knocking first.

"Come in," Toothless called from the inside.

Hiccup entered slowly and quietly, almost as if he was entering a room with a sleeping person in it. After clicking the door shut and turning around, he noticed Toothless was still looking out the window, not at him. Hiccup wasn't sure how to read that. He decided to stay close to the door in case he needed to exit quickly.

"Hi, Toothless. Um, you sent your car for me?" Hiccup was actually quite impressed that he managed to prevent his voice from cracking, squeaking, or doing anything else embarrassing.

"Yes, I did," Toothless started as he turned around. Hiccup could finally see his face, and Toothless was giving that same genuine smile that lit up his face and said he was happy to see Hiccup. At this sight Hiccup managed to breathe an internal sigh of relief. "Our conversation was cut short last time, and there is something else I want to say to you after yesterday."

And there went Hiccup's sense of relief right out the window. A nervous sweat managed to take its place almost instantly.

"Are-are you angry?" Hiccup asked, silently pleading for a no.

"Why would I be?" Toothless asked, almost amused that Hiccup would ask such a question. This just served to confuse Hiccup.

"Well yesterday, at the deli, surely you know the man I was sitting with," Hiccup started before being interrupted by Toothless.

"Yes, I know that your father is the head police detective on my case." Toothless couldn't help but smirk at the dumbfounded expression on Hiccup's face.

"How did you know that he was my father?" Hiccup blurted out before he could even think.

"Remember our first meeting how I told you I figured out your name?" Hiccup thought back and remembered the security guard or someone had given it to him. "Well he gave me your last name too, and I know all about Stoick. There may be eight million people in New York City, but I'd bet my car collection that there is only one Haddock family. The fact that I knew he was your father rather than just an uncle or something was just a calculated guess since you both have the same green eyes."

"Well I promise I haven't told my dad anything and I won't and wait a sec, how do you know my eye colour?"

"Don't worry, I believe you. And I noticed it at our first, uh, meeting, in Manhattan. You know, when I pushed you against the wall?"

Hiccup remembered that moment (and the related fear) extremely well. But in his fear, he had been too focused on the gun in Toothless' belt to notice anything else.

"Oh yeah. Then." That was all Hiccup could get out. It was silent for a few seconds, but then Hiccup got the courage to ask, "why did you want to see me again?"

"I wanted to thank you for yesterday. I noticed that your father was sitting so that he wasn't facing me. I'm guessing that wasn't a coincidence?" Toothless asked, letting the smirk from earlier return to his face and cocking an eyebrow. "But why didn't you sell me out? I mean it would technically have been the right thing to do, and you are the son of a cop."

Hiccup exhaled. "The truth is that you gave me no reason to. I mean sure you kidnapped me last time, but you did that to apologize. So I forgive you," he said, smile and confidence returning. "But that's not what I meant. I meant the first time you sent the car for me. Why did you want to see me again then?"

This time it was Toothless who exhaled, but as he did he moved and sat down in the large leather chair. As he did this Hiccup also took a seat in one of the armchairs.

"When you lead the type of life I do, anyone you come into contact with that isn't a, well, let's call them coworkers, just looks at you and practically trembles in fear. You were different. While you may have looked scared on the outside at our first encounter, when I looked into your eyes I saw amazement, wonder, whatever you want to call it, but it was the furthest thing possible from fear."

Hiccup couldn't believe what he was hearing. I mean sure the thought of seeing Toothless was cool, but all he remembered was the terror from that meeting.

"Which is why," Toothless continued, "I wanted to see you again. And now I wanted to ask you something. In my line of work, you don't meet too many people that you can actually become genuine friends with. I find you interesting Hiccup. In know friendships need time to develop, but because of my…position…I want to ask if you would even be willing to give it a try. Being friends."

Hiccup was speechless. Toothless, THE Toothless, was asking to be his friend? How should he respond? Heck, what would his answer be? He tried to form a coherent answer, but he couldn't even form a word.

He just kept spewing random sounds until Toothless finally said something. "I understand you need to take some time to think about this. So here," Toothless said as he pulled a basic flip phone out of his inside pocket. "Take this phone and call me when you have an answer. I'm the only number in there. I don't want you using your regular phone just in case your father did something to it without even you knowing."

Hiccup took the phone and tried to say something, but he was still speechless.

"Astrid will be waiting downstairs in the car you came in. She'll take you home. Take your time to decide, I'm not going anywhere."

Hiccup simply nodded and got up. He headed towards the door, opened it, but paused before stepping out. He didn't want to say goodbye because that would sound too definite, and he was still considering the friend offer, but he didn't want to say see you later either because that would imply he had already decided yes. Instead, he settled for a nod and when Toothless met that with a nod of his own, Hiccup closed the door and left.

* * *

Exactly five seconds after the click of the door had sounded, a woman in a strapless blue dress that stopped just above her knees stepped out of the bathroom. She tossed her long hair over her shoulder before going to occupy the seat Hiccup had been in not a minute ago.

"Alright Toothless, Astrid did your driving, so we're even. I don't get why you don't just hire somebody to do stuff like that for you like the rest of us do."

"You know why I don't do that, Stormfly."

"Yes, yes, but still." There was a momentary silence before she continued. "I know you want to be more than friends with that boy, Toothless. I may not have been able to see you, but I could hear you. And you had a certain something in your voice that isn't normally there. You like him, don't you? And you are trying to get him to like you back, aren't you?" Stormfly asked, a knowing smirk on her face.

"Whatever will be will be Stormfly. C'est la vie."

* * *

**Next Chapter: On or before October 4Why sooner than usual you ask? Well, you'll see when the next chapter comes...**

**As for the last line there, it's a French expression. The translation is literal.**

**Want Hiccup to become friends with Toothless? Tell him in a review! It'll mean they'll spend more time together~!**


	8. Chapter 8

**Hey everyone! I'm back already! Now if you could just remember how your feeling now and try to keep that after the ending message that would be great...**

**Also, I would like to thank the absolutely amazing Warrior Nun for doing a cover image for this story! You should all thank her since you don't have to look at my face any more XD**

**Also also, thank you again to ADAMalchemist for beta-ing. This story wouldn't be the same (or even exist at all) without you! :)**

* * *

Hiccup woke up Monday morning with a much different feeling than he had the day before. Yesterday he was fearing what the wrath of Toothless would be like, and now he was confused as to whether he should allow the man to try and become his friend. Hiccup had been kept up most of the night by that question, but he still didn't have an answer. He ended up getting out of bed at 7am because he had to get to his classes.

After the usual morning routine of shower, hair, and clothing, Hiccup entered the kitchen, and was actually surprised to see his father gone this time. Normally when Hiccup had to wake up for school his father was still there. But the fail proof signal of a folded up newspaper was there, so it was the only explanation. Although the note Hiccup found on the counter would also help.

_'Need Gobber all day today. Take the subway both ways.'_

Hiccup reread the note before coming to an executive decision. He didn't feel like going to class today, and to be quite honest he could use the time to think over the whole Toothless situation. He made breakfast a quick event this morning (cereal and milk, nothing fancy) before heading over to the elevators.

When he arrived at the elevators, he hoped that he would be able to get into the first one that arrived. As much as he didn't mind walking down all of the stairs, today he just wasn't in the mood. As if the elevator could read his thoughts, it not only arrived, but it arrived empty. Hiccup wondered if he was going to get a solo ride down too, but his hopes were dashed as the elevator stopped on each of the next ten floors, and then a few more.

Eventually Hiccup made it out of the building, but he had no idea where to go. He needed somewhere where he could go to think, not be disrupted by too many people or have too many available distractions (which was why just staying in the apartment was out), and where he could just relax. After several minutes of thinking Hiccup thought of just the spot.

He started making his way to the Grand Central – 42nd Street Station, where he waited on the northbound platform. He let the local 6 train pass, knowing that the express 4 train was scheduled to be along on the next thirty seconds. Normally since he was only going two stations up it would have been faster just to take whichever train came first, but the fact the schedule put them thirty seconds apart made the wait worth it. It arrived right on time, and thanks to the fact that it was travelling against the peak direction, there was actually a seat available for Hiccup.

He didn't know why he sat down since he was getting off at the first stop, but he sat down for the sixty second trip nonetheless. When he did get off at 59th Street Station, he started westbound to Central Park. He was headed to his all-time favourite spot in the city; a spot not even his father knew about. His mother had shown it to him, telling him that when she and his father had once gotten into a big fight when they were dating, that is where she went to get away. It was a secluded spot on the west side of The Pond in the southeast portion of the park. No trails went near there so you had to hike through the trees, but it was doable.

Hiccup stayed in that spot most of the day. Thinking, skipping stones into the water, he even climbed one of the trees. He may have been doing different things, but his mind was always on Toothless and his question, going in circles.

Yes, Hiccup knew he was a mob member, and what his father would do if he found out he was friends with Toothless. But Toothless had seemed so genuine when he said he just wanted a friend. But Toothless was suave and charismatic. He had to be to survive. Could this just be part of one of his plans? Could he be using Hiccup to get to his father? No, he was too kind to do that. But how could Hiccup know that for sure? The kindness thing may have just been an act. Toothless did look serious a lot, maybe constantly thinking about how to use Hiccup to his benefit. But that smile on his face when he saw him, the way it lit up his whole face, there is no way that could be faked, right? So he really was happy to see him all of those times. But still, Toothless was a mob member, and he kills people. What if he agrees to become friends and then an enemy goes after him to get to Toothless? No, Toothless wouldn't let that happen. But how could he prevent it? Well he did give him a cell phone for direct access to him. Plus there was still that part of Hiccup that found Toothless…"attractive". But could he really pursue a friendship for that reason? There was no way Toothless would be interested in someone like him that way. Was there?

Hiccup screamed. At the top of his lungs. It was so loud that the pigeons in the nearby trees all got scared and flew off at once in a giant cloud of feathers. Why did this have to be so hard? After a good three hours of thinking, Hiccup had finally settled on an answer. It was a bit of a compromise, but he thought that Toothless would be able to live with it. He searched his pocket until he found the little flip phone he had been given.

The phone rang exactly three times before Toothless picked up on the other end.

"Hey Hiccup!" Toothless said, sounding cheery.

"Uh, hey, Toothless. Um, I have my answer, so…"

"Wow," Toothless interrupted, "and a lot sooner than I thought. So?"

"Um, I was actually hoping we could meet in person, you know, talk face to face?" Hiccup said. Then it hit him that Toothless was probably a busy person, and that he wouldn't have time to meet like that and he probably wouldn't want to be seen in public.

After a short pause, Toothless responded, "yeah, sure," but while he tried to still sound upbeat Hiccup could tell it wasn't genuine. Before Hiccup could say anything, Toothless continued, "how about Central Park? At the Falconer Statue on the west side?"

Hiccup barely had the time to say, "sure," before Toothless said, "see you in twenty minutes," and hung up.

_'Great,'_ Hiccup thought to himself, _'I've gone and made him mad. Better not be late and make it even worse.'_

With that, Hiccup got out of the tree and headed northwest.

* * *

Hiccup arrived at the statue with five minutes to spare. After a quick glance around the general area he realized Toothless wasn't there yet, so he found himself a spot on a nearby bench and waited.

Five minutes later, exactly on time, Toothless walked up to the statue, saw Hiccup, and walked over. Toothless readjusted his suit after he sat down (this time Gucci instead of Armani) and there was a momentary silence before Hiccup started.

"So I…" was all Hiccup got to say before Toothless interrupted him.

"It's ok, Hiccup. I already know you are going to say no. It's alright. I understand. You think I'm a bad person, because of what I do, and you want nothing to do with me. But if you knew the truth then maybe you wouldn't think that." As Toothless said this his head was hung, eyes firmly planted on his black dress shoes.

Hiccup had seen both neutral and happy expressions on Toothless' face before, but never sad. He didn't even look like the same person any more. Hiccup decided that he didn't like this look on Toothless, but a part of him also wanted to know his back story. So instead of stopping Toothless and telling him that he was actually kind of going to say yes, he said, "then tell me the truth."

Toothless sighed. "The truth is that I didn't have a choice. I had to do this. When I was very young, my parents died in a house fire. Only my brother and I survived, and that was because we weren't home. But when we came home all we found was a burned out corpse of a house. Well, that, and RD. You know who that is?"

Hiccup nodded in affirmation, remembering what Ruffnut had told him, and let Toothless continue.

"At the time I was 7, and my brother was 9. We had no living relatives. Both of our parents were single children, and all of our grandparents had died. Plus we had just moved to the area and we hadn't made friends with any of the neighbours yet. RD claimed he was a distant relative called there by the authorities, and he offered to take is in. He even knew my nickname of Toothless. With nowhere else to go, we did what we thought was best. We went with him. As children we didn't think to go to the police or the neighbours or anyone. Plus we weren't exactly in the best state of mind.

He took us in and treated us like we were his own children. He brought us here, to New York. We led a normal life with him for a few weeks, but then we started to notice the strange people coming over, heard strange noises, and even a few people who came and never left. One day my brother finally had the courage to ask what was going on. RD said he respected our guts for asking, and he told us the entire truth. Including the fact that he started the fire at our parents' house. They couldn't pay back their debt to him, so he killed them. Then he told us that one day he expected us to join too, to pay back our parents' debt."

Hiccup swallowed. He had a bad feeling of where this was going.

"Again, we may have been kids, but we knew how dangerous that would be. My brother, he refused, and got really mad at RD for claiming to be family when he killed the only family we had. He said we wouldn't be dragged into that, parents' debt or not. RD said we didn't have a choice, but my brother tried to leave anyways, telling me to come with him. RD warned him to stop, that he couldn't leave because he knew too much. I couldn't move, so I just stood there watching this whole ordeal. When my brother refused to stop, RD," Toothless stopped, and when Hiccup looked over to see why, he saw a single tear rolling down his cheek. Toothless still hadn't looked up from the ground. Hiccup noticed his eyes had started to water too.

"He took out his gun and shot him. He shot him while I watched. Then, he turned to me and asked if I wanted to leave too. He had the gun pointed right at me. As much as I wanted to leave, I said no to preserve my own life. My brother was trying to get the two of us out of there, I couldn't just go and get myself killed when he had tried to save me. That would be disrespectful to him."

Hiccup noticed that Toothless was crying freely now, but his voice never hitched. In a way that was impressive. If he wouldn't have seen the tears flowing he would never have known.

"My brother is actually the reason I go by the name Toothless all the time now. It was my nickname when I was a child because my teeth came in really late. Everyone called me that, but my brother refused. He was the only person that called me by my real name. That's why no one here knows it, other than RD of course. If I heard my real name used again it would constantly remind me of him. But that's a different story. The only reason I continue to do this is because if I tried to leave RD would have no problem hunting me down and killing me. The truth is, I don't want to do this, but I have no choice. And in this life, I never really had the opportunity to make friends. You're the first person that I've actually met more than just once that I haven't had to do business with. The fact that you came back the second time, and the fact you weren't just terrified the first time gave me hope that maybe you'd consider it."

It was now that Toothless finally looked up and over to Hiccup. Fortunately Hiccup had managed to prevent himself from crying during Toothless' story, so he probably looked semi normal.

"Toothless, I am so sorry for your past."

"What are you apologizing for, there was nothing you could do." It was a true answer but it finally put a bit of a smile on Toothless' face, and that made Hiccup happy. He didn't want Toothless to have to go through any more pain today than he already had recounting that story.

"Toothless, I called you and asked you to come to meet me so that I can tell you that I am willing to try and be your friend, but I have one condition."

The smile on Toothless' face was so large Hiccup thought his face might split in half. Before he could even react, Toothless stood and was giving Hiccup a massive hug. He was strong because Hiccup had still been sitting but Toothless managed to pick him up.

For some reason, it was now that Hiccup remembered Toothless' comment about his eye colour, and he figured while they were this close would be the best time to look at Toothless' eyes. When Toothless opened his eyes, Hiccup got an up close and personal view. His eyes were one of the brightest shades of yellow he had ever seen. It was an interesting colour to say the least.

After Toothless finally put Hiccup down, he said, "anything. And I promise that I will keep you away from my work. You'll have nothing to do with it."

All Hiccup could do was smile. Smile and say, "that's all I ask."

Toothless still had that massive smile on his face. Hiccup, however, was wondering how to proceed.

"So, uh, Toothless, what do you want to do now?" Hiccup asked.

"Well, how about we really get to know each other tonight. We can go out for dinner. Katz's Deli, perhaps?" Toothless said with a chuckle. Hiccup could only shudder at the bad memory. "Kidding, kidding. How about the Redeye Grill at 7th and West 57th?"

"I've never heard of it," was all Hiccup could say.

"It's good. I've been there a few times before. How about 6 tonight?"

Hiccup couldn't think of anything else he had to do, so he agreed. He was going to wonder what he should do until then, but Toothless managed to suggest something for him.

"Great. So I'll make the reservation. And in the meantime, why don't you head back to school. You really shouldn't be missing classes you know." Toothless said that last sentence with a proud smirk.

All Hiccup could get out was a, "how did you know," before Toothless started up again to finish his explanation.

"Oh come now, Hiccup. You of all people should know that I have eyes and ears everywhere."

Hiccup realized he was right, then realized that he wasn't really upset or disturbed that Toothless had looked up his school schedule. If his father would have done that he wouldn't have been quite so passive about it. What was it about Toothless that made him so comfortable to be around? Noticing his silence, he decided he should probably say something.

"Very true. So I'll just meet you at the restaurant at 6 then?"

"How about I pick you up? Around 5:30 maybe?"

Hiccup wasn't sure how he felt about having Toothless himself picking him up right outside his condo, but he didn't want to be rude and decline.

"Uh, yeah, sure."

"Great, it's a date!" Toothless smiled.

Hiccup turned around as he called, "well, I better get to the subway if I'm going to class," and waved goodbye. He was glad he could make such a quick escape; he wasn't sure if it was a joke or not, but after that last comment Hiccup could already start to feel the blush creeping up his face.

* * *

**So there is Toothless' back story. Yeah, that's my attempt at writing sad stuff. I know, I fail...**

**Next chapter: On or before October 20 *flips table and hides behind it* I'm going out of province for school for a few weeks, but if I can I'll write! Sorry, please don't kill me D:**

**In other news, yay, Toothless is happy! But he may become sad again and Hiccup could be stood up if you don't review...**


	9. Chapter 9

**I AM SO SORRY THIS IS LATE DON'T KILL ME D:! I blame homework and House of Hades…but at least it's here now!**

**Oh, and I fell like everyone is going to hate me for what Stoick does this chapter. But remember I warned you way back in chapter 1 about his character!**

**PS Sorry if people got the notification for this twice. I just noticed an error and fixed it.**

* * *

Getting off the subway, Hiccup looked at his watch and realized he would be just in time…for his least favourite class. He considered skipping it, but then he realized that would mean his trip all the way here was an entire waste because that was his only class left for the day. As boring as three straight hours of Architectural History sounded, Hiccup decided he'd tough it out.

When he entered the classroom, he looked around for a seat and spotted Jason in the crowd. The seats on either side of him were open, so he decided he'd help himself. At least he'd have a distraction.

He sat down beside Jason, who looked up and smiled his famous smile that nearly made Hiccup's heart melt. Whiter than should be possible, and all his teeth perfectly shaped.

_'Just like Toothless'," _Hiccup subconsciously thought to himself. Before he had the chance to catch himself thinking that, however, Jason started to talk.

"Hey Hiccup! So I put the finishing touches on the house, and I think it looks great if I do say so myself."

"That's great, Jason, I'm sure it looks amazing," Hiccup said, but in his head he finished, _'just like you.'_

This got Hiccup thinking, maybe he should ask Jason if he wanted to go out sometime. He had been checking him out for a while now, so why not? Plus he seriously doubted Toothless was serious about the date thing. He was about to say something, but decided it would be best to wait until after class in case he said no so there wouldn't be an awkward air around during class.

It was then that Hiccup turned his attention back to the front of the room. Just then, he noticed a girl walk in that he didn't recognize. She was tallish, had blonde hair that was just longer than shoulder length, and actually quite good posture. She seemed to search the room before she smiled and started walking up the steps.

Jason got up when he saw her, and hugged her when she walked up to him. She ended up taking the seat on the other side of Jason.

"Hiccup," Jason started, "this is my girlfriend, Julia. Julia, Hiccup."

"So you're Hiccup! It's nice to meet you!" Julia said in a bubbly voice.

Hiccup could barely mumble out a, "nice to meet you too," before he completely left the conversation. Well, it was a good thing he decided to wait to ask Jason. He just would have been straight-zoned again. Well, at least the air wasn't awkward. Just mildly depressing.

THE LINE HERE IS THEORETICAL

Hiccup lollygagged home after class, and he ended up walking in at just past 4. He remembered Toothless would be coming for him in an hour and a half, but he figured he may as well start getting ready now so he wouldn't be in a rush later.

First thing was first, Hiccup had to look up the Redeye Grill to see what the place was like and what he should wear. When he finally navigated to their website on his phone, his eyes almost popped out of his head. This place was really nice! Well, nicer than anywhere he had ever been. But he immediately resolved that he would have to wear something nice. Plus Toothless was always in a suit, so he should at least try.

Hiccup started laying out outfits on his bed, mixing and matching dress shirts and pants that he had. He settled on pure black dress pants, a light greenbutton up shirt, and a black suit jacket on top. He ended up deciding on no tie for two reasons: he didn't have one that matched the shirt very well, and he didn't know how to tie one.

He was about to get changed, but he decided to take a shower first. It couldn't hurt, right? So after a very thorough shower he returned to his room, towelling himself off, and finally got changed into his clothes.

Hiccup had lost track of time, and just as he was holding a cologne bottle, considering if he should use it (he only used it on special occasions), his phone started to ring. It was a blocked number, and while normally Hiccup ignored them, he decided to answer it this time.

"Hello?"

"Hey Hiccup, it's me." They may have said me, but Hiccup could recognize that voice from a mile away. "I'm downstairs in the car. You almost ready?"

"Uh, yeah, I'll be down in a minute. What type of car is it?"

"Don't worry, you'll know," was all Hiccup heard before Toothless hung up. Hiccup thought he heard a smile on Toothless' voice at the end, but he paid that no mind. When the clock on his phone showed up, he noticed it was indeed 5:30. He quickly spritzed on the cologne and ran for the elevators.

* * *

That elevator ride down felt like the longest of Hiccup's life. He caught himself tapping his foot, and that made him realize that maybe he was more excited to see Toothless than he let on. Before he had time to consider that any longer, the elevator dinged, indicating it had arrived in the lobby.

The lobby was buzzing with its usual evening activity. People rushing for the elevators after a long day's work, people dressed up and heading out for a night on the town, and others just people watching from the couches. Hiccup weaved his way through the crowd until he passed through the front revolving doors.

When Hiccup got outside, he remembered Toothless' words: "you'll know." What on earth did that mean? He started to search for the Lincoln Continental, thinking that was the most obvious choice, until he heard the near deafening roar of an engine revving.

Looking towards the source of the sound, Hiccup's jaw dropped. Sitting at the curb was a Pagani Zonda, painted a deep blue so dark it almost seemed black. Hiccup was about to turn away to keep searching, but just then Toothless' words bounced around his head like an echo once more.

_'No way,'_ was all Hiccup could think to himself as he subconsciously walked over to the car. When he approached the passenger side window, it rolled down and sure enough, Toothless was sitting in the driver's seat, wearing one of his usual suits and his trademark smile. Hiccup was speechless.

"Are you just going to stand there or are you going to get in?"

Hiccup didn't realize quite how long he had been standing there, so he quickly jumped in and fastened his seatbelt. He was sure the sound the car made when pulling away turned more than a few heads. It was now that Hiccup regained his head and managed to speak up.

"So I'm guessing you weren't going for inconspicuous then…."

"What? This is a nice car and I wanted to get it out of the garage."

"And if my father had been in the lobby and noticed that car? Don't you think that that would have attracted his attention?"

"Accounted for. Your father left the station heading in the opposite direction about fifteen minutes ago. Where to though I'm not sure."

Hiccup's expression visibly saddened. "Oh, he's probably just working late again, if you know what I mean."

Toothless didn't know, but he did see Hiccup's new expression and didn't want to press the subject. Instead he wanted to inquire about his new observation.

"Uh, Hiccup, are you wearing cologne?"

Hiccup's expression went from sad to mildly embarrassed in less than a second. His face was tinged with a light shade of red. But his silence was enough of an answer for Toothless.

"Wow, didn't know that this was such a big night for you that you decided to wear cologne."

"Well, maybe I wear it every day."

"No, you don't. You've never had it on at any of our other meetings. Normally all I can smell is your strawberry shampoo."

Hiccup was actually quite impressed with Toothless' sense of smell if he could deduce that. And if Toothless paid so much attention to the little details that he could figure out what shampoo Hiccup used, he could only wonder what else Toothless knew about him.

Hiccup didn't want to leave an awkward silence in the car (although it really wouldn't be silent with the sound the engine was making), so he gave a quick, "touché."

"So, Hiccup, you ever been to this place before?"

"No. My mother always cooked when she was alive, and my dad isn't a fan of taking me out for dinner."

"Oh, I see. Well then you're in for a treat. This place is amazing."

"I'll take your word for it."

"And Hiccup, I really am sorry about your mother."

Hiccup paused. He kind of hated when people did this. It made him all emotional to think about her. Fortunately he managed to squeak out a, "thanks," and he didn't have enough time to continue thinking about her because Toothless interrupted.

"We're here."

Toothless pulled up to the valet and they both got out. Toothless tossed his keys to the valet, and told him to take extra care of the car. Hiccup could only imagine how nervous he would be if it was him giving the car keys to a stranger.

They walked up to the doors and Toothless held it open for Hiccup, before walking in himself.

The hostess, a short redhead wearing heels that where at least six inches tall, welcomed them to the restaurant and asked them if they had a reservation.

"Yes," Toothless said, "it's under the name Hiccup Night."

The hostess looked down and nodded.

"Ah, yes, here we go, table for two. Right this way please."

It wasn't a long walk; they were sitting in one corner of the restaurant, right next to the window facing 7th Avenue. After they sat down and received their menus, Hiccup finally got the chance to ask the question he had been holding in for the last few moments.

"So, Hiccup Night?"

Toothless chuckled. "Yes, well, I didn't want to use my nickname because I didn't want to raise suspicion, so I used yours. I hope you don't mind."

"No, not at all." And Hiccup really didn't. "But why Night? Why change my last name?"

"It's like I said before. I am willing to bet that there is only one Haddock family in all of New York, and I didn't want to bring any unnecessary attention. And to be honest, Night is actually my real last name, but no one really knows that."

"Oh, ok," was all Hiccup could say. He did think that it was a really cool last name.

Toothless was about to say something before a tall, dark haired man walked up to the table.

"Ah, welcome back _Hiccup_," the man said, placing extra emphasis on the name. "How are you?"

"Ah, André, how are you?" Toothless asked, shaking his hand. "Actually, this here is Hiccup. I just used his name for the reservation." André nodded and Toothless turned his attention to Hiccup. "Hiccup, this is André, one of the chefs here. He makes the most amazing steak in the city. You like steak, right?"

Hiccup nodded, and that was all Toothless needed to see before he continued.

"Perfect! Then André, we'll take two of the prime bone in New York strips, cooked medium."

"Of course! I'll personally get started right away!"

André walked off and all Hiccup could do was stop his jaw from dropping. Had Toothless just ordered for him?

"Oh, and tell Vincent to put it all on my tab, would you?"

André nodded and kept walking. Hiccup, however, started making a list in his head.

_'He took me to a VERY nice restaurant, he ordered for me, and he paid for me. This is starting to have the makings of an actual date. Maybe that joke he cracked earlier wasn't a joke. No, don't think like that Hiccup, you'll just get your hopes up.'_ Hiccup was snapped out of his thoughts when Toothless started talking again.

"So, you know all about my past from earlier today, so tell me a little about yours."

Hiccup figured he was close enough to Toothless to be able to use some of his sarcasm without having to worry. Plus if he was going to talk about his past he needed a light mood so he wouldn't be so brought down by it.

"What, you mean you haven't already used your sources to find all that out?" Hiccup asked with a smirk. Sure enough Toothless cracked a smile.

"I have to leave some things a mystery, otherwise what would we talk about?"

Hiccup couldn't help but chuckle at this. But he did have a point in a weird kind of way.

"Touché. Well, there's not much to tell." Even having said that Hiccup managed to go on for almost twenty minutes. He talked about where he was born (Queens, New York), how he was bullied in elementary school and how it just got worse after his mom died (he was nine), how his father had changed after his mom had died, and how he was dealing with his father being absent and always "working late". As he spoke he noticed Toothless paying full attention, soaking in every detail with genuine interest. Hiccup did leave out the fact that he was gay, however. Better leave that until they got to know each other better and maybe Toothless would be less weirded out. He was finishing off about school when André returned with their food.

Hiccup took one bite of the steak and thought he had gone to heaven. Toothless wasn't kidding, this guy really did make the best steaks in the city.

The conversation quickly returned, but this time it got into basics, such as favourite colours (green for Hiccup and deep blue for Toothless) and favourite spots in Central Park (The Mall for Toothless, Hiccup just said The Pond). Eventually though, Hiccup's interest in organized crime took over and he couldn't stop himself before he asked, "so how are things going with work?" He figured work would be the best thing to call it without making it too obvious.

"Oh, well, I don't know. Not too well, really."

"Why, what's up?" Hiccup genuinely did want to know, but he was also glad the conversation had shifted off the topic of himself.

"Well RD has been a little more, how do I put this, violent, lately. More attacks sooner on people not repaying debts, more shootings, telling us to use more vicious methods to get protection money, stuff like that. The other leaders aren't happy either that he is making us put ourselves in so much more danger. He's not going to be happy until someone is dead. Actually, someone is dead. Remember that guy from the night we first met? Earlier today I had to go kill him."

Hiccup was shocked. The way Toothless said that with his expression unchanging, it didn't even seem like he showed any remorse. But then again, he remembered what Toothless had seen in his life and he had been doing this for a long time. He had to stop that train of thought or he was going to get emotional.

"So, why don't you and the other leaders try to take him out? Overthrow him or something?" Hiccup asked, concern in his voice.

"If I spoke out at all against RD, or if anyone did, those loyal to him would inform him and take the individual out. I am friends with the other leaders, but you never know where their true loyalties lie. One of them could pretend to be with me, then go tell RD and get the rest of us killed. I can't be responsible for that."

All Hiccup could muster to say was a quick, "oh, wow."

"That's why I had to call in favours to bring you to the warehouse. I don't want to hire someone to work with me because I know that I would be putting someone in direct danger. I kind of feel bad bringing you this far into it," Toothless said, eyes suddenly downcast.

"It's ok, I don't mind, really. I'm sure I'll be fine. Besides, I live with my dad and it's not like I'm doing any work for you so I think I'll be fine," Hiccup said with a smile. Somehow, that logic brought Toothless back to his previous mood. Hiccup simply tossed his concerns from earlier that day to the back of his mind.

* * *

Dinner concluded well, with the remainder of the conversation just being small talk. It was when they were just getting up to leave that disaster struck.

Hiccup glanced out the window of the restaurant as he got up and watched a black Lincoln Continental pull up outside. Normally he would have paid it no mind, however the front windows were rolled down and sitting in the driver seat was Gobber.

Hiccup's heart started to pound, and he felt clammy, weak, and dizzy. He must have really been flushed because Toothless suddenly became concerned when he saw him.

"Hiccup? You don't look very well. Are you ok?"

Hiccup almost had the strength to answer, but then the situation went from bad to worse. Gobber looked over into the restaurant and his eyes widened exponentially when he saw Hiccup. Toothless was hidden behind a bush until he came over to Hiccup to see if he was alright, and when Gobber caught a glimpse of him, his jaw dropped. He regained enough composure, however, to quickly mouth, "sorry," before rolling up his tinted window.

Hiccup's attention then turned to the back door of the car, which had just opened. By this time, Toothless too was looking at the car, hand on Hiccup's shoulder and wondering why he was staring at it the way he was.

Stoick started to get out, followed by two girls that Hiccup didn't even bother to look at long enough to get a description. He did see his dad flex for one of them though and watch them giggle, and that almost made Hiccup physically sick.

By now Toothless understood exactly what was going on, and he also realized that with the state Hiccup was in he probably wasn't going to move anytime soon.

"Hiccup, this way," was all Toothless said before he grabbed his wrist and started pulling him towards the kitchens.

Fortunately Hiccup was conscious enough to realize Toothless was taking him away, so he didn't end up tripping or falling. He kept his head down as Toothless weaved with him through tables, a door, the kitchens, and out the back way into the alley behind the building. The entire walk Hiccup's heart had felt like it was being compressed, and now that it was just the two of them he felt like he could let it all out.

Hiccup started bawling, and Toothless wrapped his arms around Hiccup and pulled him close. He whispered sweet nothings until Hiccup had calmed down a little.

"Almost every single night he does this. He goes out to clubs and picks up these women. And then he treats them better than me even though the next time he'll have someone new," Hiccup said between sobs.

Toothless couldn't help but feel bad for him. "It's ok Hiccup. Let it all out. Things will get better, I promise. They always do."

Hiccup looked up at Toothless and saw him trying to smile despite the situation. Maybe he was right. Things just might get better. And if Toothless was around he didn't doubt that they would.

It was then that reality hit him. He may have had a crush on Jason, but as Hiccup looked into Toothless' yellow eyes while being held in his arms, he realized: he really was falling in love with Toothless.

* * *

**Yes, I use the word straight-zoned in real life too XD And I'm sorry I didn't respond to any of the reviews from last chapter, but I've just been so busy...I barely had time to write this!**

**Next chapter: On or before October 31 (blame the homework D8)**

**Quickly! Write a review to distract Stoick so Hiccup and Toothless can get away unnoticed!**


	10. Chapter 10

**HAPPY HALLOWEEN! What are you dressed up as? Tonight I'm Nico Di Angelo. If you know who that is you're amazing. If not, perhaps it's time to check out Rick Riordan...**

* * *

"Come on, I'll take you home," Toothless finally said after the momentary silence.

After leaving enough time to be sure that Stoick was inside the restaurant, Toothless and Hiccup walked back around the front and got his car from the valet.

The ride back to Hiccup's condo was silent, but it wasn't an awkward silence. It was the kind of silence where everyone is lost in their own thoughts and everybody knows that. Hiccup was thinking of his recent revelation, while Toothless was thinking about how bad he felt for Hiccup's situation. It was only when Toothless pulled up to Hiccup's building that they were brought out of their thoughts.

"Thanks for tonight," Hiccup started, "it was actually a lot of fun until, well, yeah."

"Yeah. Sorry about that."

"Why are you apologizing? You did nothing wrong."

"I don't know, just seemed like the right thing to say," Toothless said with a smile. "So, will I get to see you again soon?"

Hiccup smiled that smile he had when he had a good comeback and stated, "Something tells me that even if I said no I wouldn't have much of a choice when that black Lincoln shows up. But yes, definitely."

"Goodnight Hiccup," Toothless chuckled.

"Goodnight," Hiccup responded before closing the door.

Toothless watched Hiccup walk through the main doors before he drove off.

* * *

Toothless didn't need that long to get back to his condo in the Upper East Side. After parking his car in the underground he headed for the elevators to head up to his 19th floor condo.

There were only two condos on the floor, one of which was Toothless'. Oddly enough he never saw his neighbours. He unlocked the door and shut it behind him, not even turning on the lights. He started to walk through the condo, knowing where everything was without the lights. He started heading to the far back corner to the living room, deciding to watch a little TV before going to bed. He passed the large kitchen, formal dining room, and full bath, as well as the stairs heading up to where the three bedrooms and two additional bathrooms were. In total the condo was about 2000 square feet, almost the size of a house. And that was why Toothless loved it; it had the space of a house with the location and amenities of a condo.

He entered the living room, but stopped just before turning on the lights. Taking in a deep breath, he said, "You know Stormfly, that key I gave you was just for emergencies."

It was then that he flicked the lights on and Stormfly stood up from a large armchair facing the opposite direction.

"There was no way you saw me. What gave me away?" she asked, slightly disappointed to be discovered so easily.

"Your perfume. It's quite unique."

She chuckled at this. "Well I should hope it is, I have it imported from South America. They don't sell it here."

"Why do I have a feeling you are here to discuss more than just perfume?"

"Right to the point hm? Fine. I know you went on a date with that Hiccup boy."

"Really? Spying on me?" Toothless asked, sitting on the couch. Stormfly returned to the armchair from which she had stood and straightened her dress. It was blue like the last time Toothless had seen her, but was of a different design, with a strap over one shoulder.

"Well when you go to a restaurant in my district and under my watch odds are I'll find out about it," she said with a smile.

"Remind me to thank Vincent later. But anyways, it wasn't really a date. More of a get to know each other session. Besides, I don't even know if he's into guys."

"Oh of course it was a date," Stormfly scoffed. "You clearly like him, he clearly has feelings for you even if he doesn't realize it, and you took him to a really nice restaurant. That's a textbook date if you ask me."

Toothless listened, but had zoned out part way through the sentence.

"How would you know if he has feelings for me?"

Stormfly held back her smile. She had been bluffing Toothless. She didn't know for sure if he had feelings for Hiccup, but the fact that he had zoomed in on that part of the sentence confirmed it enough for her.

"Call it a woman's intuition. But regardless, I think it went quite well. Except for maybe the ending. But I think that actually helped you in a way."

Toothless was confused by this statement, and Stormfly clearly wasn't going to help. She had already called out a farewell and was halfway out the door.

Toothless decided to skip out on the television and go straight to bed. Between his time with Hiccup and Stormfly's riddles, he decided he'd had enough drama for the day.

* * *

Two days had passed. Hiccup had been expecting to see Toothless sooner than this, or at least get a phone call.

_'Great. I hope I didn't blow my chances with him,' _Hiccup thought to himself before he suddenly stopped in the middle of getting dressed. He wasn't sure if he had meant that in a friendship way, or as in something more. He shook the thoughts from his head. He didn't even know if Toothless was into guys. Probably not.

When he finished getting dressed, he walked over to his desk to grab the papers he needed. While shifting papers around, the cell phone Toothless had given him a few days back became uncovered. Hiccup considered calling Toothless, but he didn't want to interrupt him if he was in the middle of something. And considering he hadn't made contact in two full days that was very possible. He put the phone in his pocket anyway.

Skipping breakfast today, Hiccup went downstairs and found Gobber waiting for him. Surprisingly, Gobber had been driving Hiccup both ways to and from university for the last two days. Also surprisingly, he hadn't made any mention of the restaurant.

"Morning Hiccup," Gobber said as Hiccup closed the door. "So, it's been two days. You going to tell me what was going on at that restaurant?"

Nevermind.

"I assure you I have no idea what you're talking about," Hiccup said, hoping Gobber would drop the subject. No such luck.

"Don't give me that. I saw you in that restaurant with Toothless. You want to explain?"

Hiccup knew that Gobber wouldn't go to his father even if he continued to refuse, but he figured he kind of owed the man something. He was just concerned for him.

"Ok, yes, we had dinner together. We are friends. I finally have a friend, and it is the man that my father wants to put behind bars. Happy?"

Hiccup immediately felt a twinge of regret within himself. Gobber had never been anything but nice to him, and he had just kind of snapped at him.

"I'm not going to criticize your decisions Hiccup, even if I don't agree with them. Just promise me you'll stay out of trouble?"

"Yes, Gobber."

After that, the car ride was silent.

* * *

Hiccup sat through his History of Northern Europe class but wasn't really paying attention, and not even Jason in Design Studio could take his mind off of Toothless. In fact, the last few days Jason had been becoming less and less distracting to Hiccup. Hiccup figured it was a by-product of his discovery a few days back.

During his break, Hiccup held Toothless' phone in his hand the whole time, practically willing it to ring. Hiccup continued his day as usual, trying not to let the phone distract him too much.

While Hiccup was sitting in his History of Organized Crime class, it happened. His professor was talking about the Fire Breathers gang, and more specifically about a suspicious shooting that had happened exactly a week ago where the man had been shot in an alley in the knee caps over on East 32nd Street. Hiccup was already trying hard to keep his expression neutral (he remembered that shooting VERY well), and he almost faltered when Toothless' phone rang and his caller ID showed up. Having forgotten to put the phone on silent, Hiccup quickly pushed the reject button and hoped Toothless wouldn't be mad; he'd call him back after class.

* * *

Class ended early and Hiccup exited the building, phone in hand and ready to call Toothless back. However, he didn't even have the time to push send before he heard a familiar voice call his name. When he looked over, Toothless was standing there waiting for him.

No one seemed to take notice of Toothless which was fine with Hiccup as they started to walk north.

"So, what are you doing here?" Hiccup asked.

"You didn't answer the phone, so I was concerned. Thought I'd stop by to make sure you were alright."

"How did you know where I was?"

Toothless smiled. "You've already forgotten that I have connections at the university and know your schedule?"

Hiccup let a bigger smile grow across his face. Toothless had walked right into his verbal trap.

"Then you should have known I was in class and wouldn't answer my phone."

This time it was Toothless' turn to say, "Touché." After a momentary silence, he continued.

"So I wanted to apologize for the sudden cut off of communication. It's just that word of the shooting where we met has gotten out, and the police are trying to pin me to it. In fact I had a lovely sit down with your father on Tuesday. So I've been laying low for the last few days."

"Did they have any evidence?"

"No, I always make sure that I leave no evidence. It's kind of my specialty."

"Well that's good then. And actually, my prof was just talking about that shooting. I had a hard time keeping a straight face."

"I could imagine."

"But can I ask you something Toothless?"

"Anything."

Hiccup wondered if that was a legitimate offer or if he was just using it as an expression. In his eyes he seemed genuine but Hiccup guessed if he was serious about his promise to keep him out of danger that he wouldn't answer anything.

"Why don't you have anyone working with you? I mean Barf and Belch have Tuffnut and Ruffnut, why don't you have anyone like that?"

"It kind of goes off what I said at dinner. I couldn't bring anyone directly into this. I couldn't be responsible for ruining a life like that. And plus if anything ever happened to them, I don't know what I'd do."

Hiccup was stunned to near silence. Toothless was right, he had essentially said this at dinner a few nights back and he been around Toothless a few times, but it was just hitting Hiccup now how caring and selfless Toothless really was.

Small conversations continued as they continued walking and talking. Hiccup was amazed how easily he could talk with Toothless about almost anything. It wasn't long before Hiccup had lost track of where they were and he noticed they were all the way in the Upper East Side. It was Toothless that remarked on their distance first however.

"Wow, we made it really far. Have you eaten yet?"

"No, I haven't. But it's ok, I'm not really hungry," Hiccup responded.

"Are you sure? This is actually my building, you could come in if you want and we could have a bite."

Hiccup's jaw nearly dropped. Of course Toothless lived in the fanciest building in one of the nicest parts of the city right next to Central Park.

"Thanks, but I have to get home." Right as he said this, Hiccup's face drained of colour. He had forgotten that Gobber was expecting to pick him up at the university. Toothless took notice of his panicked look and became immediately concerned.

"Hiccup, what's wrong?"

"My dad's driver is expecting to pick me up at the university. If I'm not there I don't know what'll happen."

"I'll drive you back. Come on," Toothless said while leading Hiccup into the building and down to the underground parking lot.

They got into Toothless' Land Rover and Toothless started back towards the university. The ride was silent for Toothless, but Hiccup's heart was pounding in his ears and his mind was racing with possibilities of what would happen if he didn't show up. Would Gobber get fired for losing Hiccup? Would Gobber tell his father about Toothless thinking that something had happened to him? He didn't want to think about it.

Fortunately the lights were with them, the traffic was light, and the class had ended early. When they arrived back at the university, it was just fifteen minutes after the class would have ended. Hiccup thanked Toothless and jumped out, knowing Gobber would be waiting around the corner.

Sure enough, as soon as Hiccup rounded the corner the Lincoln came into view. He jumped in, buckled up, and Gobber drove off.

"I wasn't sure you were coming!" Gobber said.

"Yeah, sorry, the prof kept us late and," Hiccup started, but the look Gobber was giving him in the mirror made him stop. "What?"

"I saw you walk off with Toothless." Hiccup looked down and he continued. "I'll say again I'm not going judge but please stay out of trouble. And I'm not going to go to your father. What you do in your life is your business. You're an adult now. And next time if you're going to wander off, just message me and I'll deal with Stoick. You don't have to come all the way back. Got it?"

"Yes, Gobber. And Gobber?"

"Yes?"

"Thank you."

* * *

**Next chapter: On or before November 3. I'll be nice after these large gaps.**

**I legitimately want to know what people dressed up as today. Let me know!**


	11. Chapter 11

**I know I'm late I'm sorry please don't kill me D8**

* * *

Hiccup loved having Fridays off. He could "sleep in" (until 8:30, what a rebel), and then he had the entire day to do what he wanted. For this Friday, however, the fates had decided to make plans for Hiccup. Or at least Toothless did.

It was 10:00 when Hiccup was swallowing his last bite of breakfast and the phone Toothless gave him rang. He swallowed the last of the food in his mouth and hastily answered.

"Hey Hiccup. I was wondering if you wanted to go out tonight. There is this really cool night club here in Manhattan that I love and I think it would be fun."

Hiccup nearly stopped breathing after the "go out tonight." Of course his mind went straight to making it sound like a date. He had to remind himself that friends say that too, and if he wasn't going to wreck this friendship then he better not keep messing up like that.

"Uh, Hiccup? You still there?"

That snapped Hiccup out of his daze. He hadn't realized just how long he had been silent.

"Uh, yeah, sure," Hiccup said without really thinking. Then it hit him. "But Toothless, I'm only twenty. I'm not old enough to get into a club, remember?"

"Don't worry, I remember. I also have a plan. Are you doing anything right now?"

"No, I don't have any plans for right now. Why?"

"Good. Go outside, I think you'll see a familiar car waiting for you."

"Well, at least this time I know I'm going to be ambushed outside my building," Hiccup said with a twinge of sarcasm.

"Yeah yeah," Toothless chuckled, "just come on."

Toothless hung up and Hiccup just grabbed his jacket and keys before heading downstairs, practically sprinting to the elevators. He was actually quite excited for today now. On the way down he was having a little bet with himself as to who would be driving the car. He figured it would be Astrid. Since he would be coming willingly the two twins wouldn't be needed.

Sure enough, right outside the building door was a black Lincoln Continental. He opened the door and got in, only to find his guess was wrong. It was actually Toothless driving this time. It took him a couple blocks to get over his surprise, and Toothless said nothing until Hiccup did.

"Well, I never thought I'd see you driving something as lowly as a Lincoln," Hiccup cracked from the back seat.

"Why not? I needed a car you'd recognize for sure and I currently don't have any favours to call in."

"Trust me, I think I would have recognized any car from your garage."

Toothless was about to respond when his phone started to ring. He hesitated a moment but did eventually glance down to see the caller ID.

Expression becoming deadly serious, he turned to Hiccup and said, "I'm sorry Hiccup, I really have to take this. You don't mind do you?"

Hiccup couldn't refuse. Toothless was using his deadly serious expression, that one you just know not to say no to. Not that he would have anyways. If Toothless didn't answer his phone and it was someone important they may realize he is being preoccupied by someone.

"No, of course not. Go ahead."

"Thanks. And do me a favour? Try to be as silent as possible."

Hiccup just nodded. OK, this was officially kind of scary. He even noticed that he had subconsciously started to slow down his breathing a little bit.

When Toothless did pick up, it was the weirdest phone conversation that Hiccup had ever heard. He couldn't hear the person on the other end, and the whole time Toothless didn't say a single word. Just affirmative grunts every now and again. After a few minutes Hiccup gave up trying to eavesdrop whatsoever. He almost sighed in frustration but he remembered what Toothless had said about being quiet at the last minute. He ended up twiddling his thumbs and staring out the window at the blurred view of New York, but then it hit him. What if Toothless was suddenly called somewhere and because he was in the car he would have to go with him? A nervous sweat broke out across his forehead and his legs started shaking. He promised he wouldn't drag Hiccup into anything, didn't he? Well, all Hiccup could do now was wait and see.

* * *

Toothless was on the phone the entire way to the warehouse. Hiccup actually felt a sense of relief when he saw it, realizing they were most definitely headed to a familiar destination. The nervous sweat stopped when they turned onto the property, and his legs stopped shaking once they were parked in the massive garage. Toothless had hung up just before they had parked, but Hiccup did not want to be the person to say the first word. What if that phone call had put Toothless in a bad mood? Fortunately he didn't have to wait long for his answer.

"Sorry about that," Toothless started, the smile returning to his face. "Important call. But that should be it for the day. So no more distractions before tonight."

Hiccup wondered what he meant by "before tonight", but he just shrugged it off. But that reminded him.

"Yeah, about tonight. I'm still too young for a club. What exactly is your oh so masterful plan?" Hiccup asked wryly.

"Have a little faith in me," Toothless said, smiling at Hiccup's tone. "Come on. This way."

As they were walking, they passed the mechanic working on the underside of the Bugatti, and something Toothless had said came back into his mind.

"Hey Toothless, if you don't want anyone working with you, why do you have a mechanic hired? And how do you keep this place so clean?" Hiccup asked, wondering about the contradiction.

"Oh, well, technically the mechanic doesn't work for me. He works for a garage that will send mechanics out to people's homes to repair and maintain cars. He's only here once a week or so, and mostly he's quick. Just like the cleaning company I hire."

"But the very first time I came here, with Ruffnut and Tuffnut, he came out of the garage to make sure I was the right person, and actually Ruffnut slapped him," Hiccup responded, confused.

"Really? She slapped him? So THAT'S why he was so mad after that," Toothless said, sounding like this was some great discovery. "But yes, he was working when you were supposed to get here so I just asked him to make sure not to let anyone in unless I approved them. I say it's for the security of the cars."

"So you're the only person who is always here? Seriously? Doesn't it get lonely?"

Toothless let out a sigh before responding, and Hiccup took this momentary lapse to realize they had already climbed the stairs and were in the hallway that led to Toothless' office, among other places he had never seen.

"Sometimes. But that's why I try not to spend much time here. This is mostly just a neutral place to meet people and a storage facility for some of my machinery. Like this," Toothless stated before coming to an abrupt stop in front of one of the doors. While Hiccup couldn't tell which one it was, and he wasn't sure how Toothless could either, he knew it wasn't Toothless' office because it was on the wrong side of the hallway. It actually kind of excited him, getting to see behind another one of the mysterious doors.

Toothless opened the door and walked in, Hiccup right behind him. It was smaller than Toothless' office, most likely about 150 square feet, and all of the walls were perfect white. No other colours, no markings, not even a picture hanging off the wall. Situated in the middle of the room was a fairly large, dark grey machine. Hiccup had no idea what it did as he had never seen anything like it before. There was also a camera and a tripod sitting in one corner.

"Alright, go stand over by the wall near the camera," Toothless said while walking up to the machine and pushing a few buttons. After a few seconds, Hiccup walked where he was told to and waited.

Toothless came over and picked up the camera.

"Alright, say cheese."

He snapped the picture before Hiccup could even react, but Toothless was already smiling at it on the digital screen, so he assumed it was fine. He kept quiet as Toothless plugged the camera into the machine and started typing on the other side. Walking around Hiccup discovered there was a computer attached on the side that he hadn't seen. He couldn't quite see the screen from his angle, but he didn't think anything of it. He glanced around the room, looking for something to do while he waited for Toothless, but there really was nothing. The walls were all the same shade of white, there was also nothing on the back wall that Hiccup hadn't seen before, there were no windows, and the only furniture was what Hiccup had already seen. He ended up just leaning in a little closer to the machine to try and figure out just what exactly it did.

He kind of wanted to touch it, but it suddenly started to whirr and it took some effort to hold back his very manly scream. Toothless stood up from the computer and walked up to the side of the machine that had a little door on it.

"Hey Hiccup, come here and watch this."

Hiccup obeyed, standing right next to Toothless (the arm brush may or may not have been intentional). They stood there in silence for about thirty seconds. Hiccup was about to ask what they were looking at, but the machine ding beat him to it.

Toothless opened the door and pulled out a small rectangle of plastic. Hiccup gave him a confused look before he got a closer look at it. It was an exact replica of a New York state drivers licence. His eyes scanned the newly formed counterfeit identification and noticed only two differences from his real one: his address had moved to the upper east side, and his birthday was now two years before his actual one.

"Looks good doesn't it?" Toothless asked. "Just don't forget to sign it." Toothless clearly wasn't even trying to hide the smile on his face.

Hiccup still had a few questions buzzing through his mind.

"So, you have a machine in its own room just to make fake IDs?"

"It can make a few other things too." Toothless semi-defended.

"Ok, whatever. But what's with the new address?"

"Oh, I figured that it would be best to associate you as little as possible with your father just in case."

"I guess that's clever. But where is this place?"

"It's my condo."

Hiccup was about to respond but he was interrupted by the machine dinging again. He hadn't even noticed that it was still running. Toothless opened the door again and immediately pocketed the other piece of plastic.

"Uh, Toothless?" Hiccup asked.

"It's just an extra copy, just in case," Toothless said with a smile. Hiccup dropped it there, he had no reason not to believe him.

Hiccup inspected the drivers licence once more before Toothless announced that he wanted to head back to Manhattan. There was nothing left that he needed to do in the warehouse and he didn't really like being there more than necessary.

They walked back to the garage together, but Hiccup stopped once he got inside. He was ready to head to the Lincoln, but Toothless hung a right and started walking the other direction.

Hiccup jogged to catch up with him and they stopped next to a passcode sealed box. It was a big grey square, approximately 60 centimetres wide and tall and about 7 centimetres deep.

"Uh, Toothless, what is this?" Hiccup asked, a little confused as to what was going on.

Toothless didn't answer, but instead entered the passcode. Hiccup courteously averted his eyes even though Toothless had made no attempt to hide the buttons he was pressing.

When he heard the ding Hiccup figured it was safe to look again, and sure enough the door was open. Inside had to be about 2 dozen sets of keys.

Hiccup was interrupted from his observing when Toothless finally said something.

"Pick one."

"Sorry?"

"Pick a key Hiccup," Toothless said with a smile.

Hiccup walked up to the box. They all looked pretty much exactly the same. Hiccup figured these were all the keys for all the cars in the garage, but they didn't even have the car manufacturer's logo on any of them. Maybe Toothless had generic copies made for security.

Hiccup picked a key and shut the box's door afterwards. Toothless, still smiling for some reason, grabbed Hiccup's wrist and said, "Come on."

They walked to the centre of the garage, where there was a painted dot on the ground Hiccup had never noticed before. When they got there, Toothless told Hiccup to hit the lock button on the fob, and Hiccup obliged. When he did they both instantly turned to see where the beep was coming from.

Hiccup didn't notice which car it was, but clearly Toothless did. Once again Toothless grabbed Hiccup's wrist (not that he was complaining or anything) and dragged him over to the Bugatti. Sure enough, when Hiccup pushed the unlock button this time, the car's lights turned on and there was a small clicking sound of doors unlocking. Looking around, Hiccup saw the mechanic was gone.

"Alright, nice choice Hiccup. Let's go!" Toothless said before heading over to the passenger side of the car. This confused Hiccup.

"Oh, is it a right side drive?" Hiccup asked, not sure of why else Toothless would go to that side. He definitely wasn't prepared for what Toothless said next.

"What? Oh, no. You're driving."

Hiccup actually fell over. He didn't know how or why, but he did. Toothless instantly ran over and knelt beside him, asking if he was ok, but Hiccup just waved him off.

"I'm fine. But why am I driving?"

"Because why not?" Toothless stated with that same amazing smile. Yup, looked even more amazing up close Hiccup thought to himself.

"Well, can't argue with that logic," Hiccup responded as he got up and walked to the driver's seat. When they both got into the car, Hiccup buckled up and put the key in the ignition.

The sound of the Bugatti's engine coming to life was nothing like Hiccup had ever heard before. It sounded so powerful it almost scared him. It almost scared him as much as the thought of what would happen if he accidentally crashed the car while driving it. Finally, however, with Toothless' silent encouragement of smiles and nods, Hiccup gathered the courage, put the car in gear, and slowly started forward.

* * *

**And how nervous would you be driving a multi million dollar car owned by someone else? XD**

**Next chapter: On or before November 11**

**Your reviews are calming to Hiccup's nerves. Help calm him so he's less likely to have a panic attack and damage the car. Don't make Hiccup beg...**


	12. Chapter 12

**To my fellow Canadians: I hope you remembered your poppy today.**

**To everyone else confused by that: In Canada today is Remembrance Day. It is the day we remember those we lost in past wars and thank our veterans and those who continue to keep the peace today. It is today because World War 1 ended on the 11th hour of the 11th day of the 11th month, and we wear a poppy because of the poem "In Flanders Fields" by John McCrae (a Canadian). The poem is very beautiful and if you've never heard of it before you should Google it.**

* * *

Hiccup had finally started to gain a little confidence in himself. He was just getting used to the handling of one of the most expensive and most powerful cars in the world, and then he saw the highway. Multiple scenarios of fiery crashes ran through Hiccup's head simultaneously. His nervous must have started to show because Toothless said something at this point.

"Hey, it's fine. You'll be fine. Besides, the car is fully insured." That last part he said with a smile. Hiccup was amazed just how much Toothless clearly trusted him. A little bit of his confidence returned, but if Toothless would have looked close enough he would have seen Hiccup's legs were still slightly shaking due to his nerves.

Fortunately for Hiccup's stress levels, the highway was jammed almost right away and all the way into the city so he got to drive slowly.

When they were finally going through the tunnel into Manhattan, Hiccup said, "I think it'd be best if we just took this straight to your condo. People might notice me getting out of a car like this and start asking questions."

"Alright, if you're sure. Do you remember the way?"

"No, not entirely."

Toothless gave Hiccup the directions and soon enough they were at Toothless' place. Hiccup very carefully parked in the underground and they took the elevator to the lobby, where Hiccup returned the car keys.

"So, when do you want to meet?" Hiccup started.

"Well," Toothless thought, "it's 4 o'clock now, so how about I pick you up at 9?"

"Sounds great. I'll see you then," Hiccup said before walking out the door.

'_OK, so I have 5 hours to get home and get ready,' _Hiccup thought as he started the walk to the southbound subway station. '_I wonder if I'll run into dad at the apartment.'_

* * *

Hiccup did not run into his father at the apartment. He ran into him in the subway. Now that was awkward. Fortunately they did not have to speak to each other as they were on opposite platforms, but there was an awkward staring contest. Hiccup was left wondering what on earth his father was doing in the subway. Where was Gobber? And there was no way he was confusing him with someone else because no one else in New York City looked like that; Hiccup would bet a lot on that.

When Hiccup returned to the obviously empty apartment, the first thing he did was go to the shower. He needed to get all of this nervous stress sweat off of himself. He enjoyed a long, warm shower, and today the water was the perfect temperature. After finishing washing himself he just stayed and let the warm water cascade over his body. Hiccup did this sometimes; he just stood in the shower and pondered life. His thoughts wandered to school, his mom, and eventually to Toothless. It was after a moment or two on that last subject that Hiccup decided it was best to get out of the shower.

Hiccup spent a ridiculous amount of time trying to figure out what to wear to the club. He had never gone to a club before so he had no idea what people wore. He even got desperate enough to google it at one point, but all the different results he got did nothing but confuse him further. Toothless didn't say which club it was or how nice it was, so Hiccup really had to be ready for any situation.

After walking around and thinking in his boxer-briefs for another few minutes, staring at his closet and all the clothes dangling therein, he finally decided. He grabbed a pair of extremely dark wash blue jeans, a light blue button up shirt, and a plain white t-shirt to wear under the blue shirt. He couldn't decide whether or not to button it up, but in the end he decided it did indeed look better buttoned. He completed the outfit with a pair of plain black dress shoes. Fortunately it wasn't supposed to be too terribly cold that night so he didn't think he'd need a jacket.

A quick glance at the clock on his desk showed the time was only 6:30, and Hiccup's stomach rumbled as if to confirm it was dinner time. Hiccup walked to the kitchen, but didn't want to eat much. Mostly because he was worried that if he had to prepare something he would splatter on his outfit and need to pick out another one. In the end his simple solution ended up being a little yogurt and a few crackers. Not much but it stopped his stomach from rumbling.

Hiccup decided to use the two hours he had left to do his homework. Basically just some math for his physics class. Generally it was peoples' worst mark in the architecture program, but Hiccup actually quite excelled at it. Although he may have made a few mistakes this time because as it got closer to nine he slowly got more and more excited. When he finished he glanced at his phone to see the time, but just as he read 8:59, Toothless' phone (which had been sitting on the table) started to ring.

Hiccup jumped up, dropped his normal phone, picked up Toothless' phone, his wallet, keys, and the fake ID and bolted towards the door. He didn't even lock the door in his excitement. It had barely even been five hours but he was really excited to see Toothless again.

After the phones fourth ring, Hiccup decided it would be best to at least acknowledge Toothless, so he picked up, gave a quick, "on my way," and hung up again. Hiccup was pretty sure that this was the slowest elevator ride of his life.

When he finally did reach the bottom floor (ten stops later), Hiccup made sure he was the first person out of the elevator and sped to the front doors. In his haste, however, he did manage to keep an eye out to make sure his father was nowhere to be seen.

As Hiccup suspected, Toothless was there in the Bugatti. He walked over and jumped in, trying to hide the fact that he was perhaps a little too overzealous from Toothless.

"Wow, excited much?"

Well, that failed.

"Just a little. Don't judge, it's my first time going to a club. I'm excited to see what it's like," Hiccup defended.

"I'm not judging! I remember my first time too. It was a little awkward at first but in the end it was a lot of fun," Toothless said with a completely straight face. Hiccup, as soon as Toothless had said that, was trying to determine if the double entendre in the sentence was intentional or an accident.

There was an abnormally large number of pedestrians on the street that night, so Hiccup didn't say much as to not distract Toothless while he was driving. It didn't take long though before they pulled up to a building on East 54th Street and Toothless stopped the car. When they got out, Hiccup was shocked to see Astrid standing there waiting for them. Toothless, however, was not.

"Astrid, nice timing. Just back to the warehouse please," he said as he tossed her the keys. Astrid didn't say a word, she just nodded and got to work.

As Hiccup was distracted, he didn't notice Toothless come up beside him until he had his arm around his shoulders. Hiccup supressed the surprised noise that was forming in his throat but he could definitely feel the start of a blush with Toothless being this close.

"Welcome to Lexicon Night Club Hiccup. Come on, let's go." Toothless said as he started pulling Hiccup forward with him.

"Uh, Toothless, there's a line, don't we have to wait?" Hiccup asked, confused.

"Not when you're on the list," Toothless smiled. With his arm still around Hiccup's shoulder they bypassed the line and walked right up to the bouncer. Hiccup could already feel the vibrations from the music inside the club.

The only thing the man did when they walked up was point to Hiccup and mumble, "ID."

If Hiccup had any type of cool before this point, this is where he came closest to losing whatever he had. Suddenly he was extremely nervous. What if the guy knew it was a fake? Would he call the cops? Would his dad find out? Not wanting to seem suspicious by delaying, Hiccup pulled the ID out of his pocket and handed it to the bouncer, barely managing to keep his arms from shaking. Toothless must have noticed something was wrong because he squeezed Hiccup's shoulder and gave him a look of concern.

As it turns out, Hiccup's concern was all for naught. The man just barely glimpsed at the piece of plastic before handing it back and opening the rope barrier without a single word. That started to ease Hiccup's nerves, but they shot right back up again inside the club. Toothless had gotten them a private booth, and right after they sat down, more scenarios started running through his head. What if he ordered a drink and the bartender or whoever asked for ID again but realized it was a fake? What if someone was watching the security cameras and noticed he was underage? To anyone these concerns would seem at least partially irrational, but to Hiccup they were entirely real.

After a few minutes Toothless got them a couple of drinks and they started chatting about nothing in particular. The music was really loud though so they had to lean in really close to each other to be able to hear, not that Hiccup minded. Hiccup took his first sip in the middle of one of Toothless' sentences and was actually surprised. This was his first time having alcohol, and he had heard that sometimes the first time you have it it tastes disgusting, but this actually tasted really good.

After the second drink Toothless asked Hiccup if he wanted to go on the dance floor and dance a little, but Hiccup declined saying he wasn't a very good dancer. Toothless scoffed at the excuse but dropped it at the time.

After the third drink Hiccup felt like he was relaxing a bit and he was really enjoying the conversation with Toothless. He stopped constantly glancing over to the door and the security cameras. He probably knew where every camera in the room was at that point. It was at this point that Toothless also reminded him to watch how much he drank. The first time a lot of people don't realize until it's too late. Hiccup promised he would and Toothless dropped the subject, hoping Hiccup would know his own limit.

After the fourth drink (and the first shot) of the evening Toothless had finally gotten Hiccup to just get up and go out on the dance floor. Hiccup was stiff at first, but with a little encouragement from Toothless he got going a little. Although even after he got going Toothless stayed abnormally close to Hiccup. If he didn't think Toothless was straight he would have thought he was almost flirting with him with how close he was. But that was a ridiculous thought. Right?

After the fifth drink (also a shot) of the night which was drunk on the dance floor, a girl came up to Hiccup and started dancing with him. She was shorter than average but wore excessively tall heels to make up for it, was in a little black dress, and had wavy brown hair that stopped around her shoulders. He sort of turned away but at the same time he didn't want to be rude by just ignoring the girl. He also noticed Toothless had moved away from them so he chatted with the girl momentarily but then told her that he had to go back to talk to his friend. Fortunately she got the message and left him alone, and Hiccup was relieved that she didn't look upset. Instead of going over to Toothless though he went back to their booth, and Toothless followed him.

After the sixth drink (again a shot) they were back to chatting.

"I saw you dancing with that girl," Toothless said, giving Hiccup a smile.

"Yeah," was all he got in return.

"Why didn't you talk to her? I think she thought you were good looking," Toothless asked with a wink at the end.

"Well," Hiccup started, not sure of what to say, "she wasn't really my type."

"Oh. Well what is your type?"

Before he had the chance to answer, they were brought two more drinks from the bar. Hiccup took a sip, and he didn't know what it was about that one drink that set him off, but suddenly he didn't care anymore.

"Guys."

Toothless needed a moment to register that, but even after that he didn't respond right away. The first thing that went through his mind was, '_Wow, so Stormfly was right_ _about that._'

Realizing he had stayed silent and not wanting Hiccup to think that he was disgusted or anything, he decided he needed to say something. He would have told Hiccup that he was gay too but he thought that may have seemed a little awkward. In the end he just said, "Alright, cool," before changing the topic once again.

They continued to chat about less sensitive topics through drink eight, and they only stopped talking half way through drink nine when Hiccup made the conversation take a sharp turn.

"What time is it?" Hiccup asked seemingly out of nowhere.

Toothless looked at his watch before responding, "just past one, why?"

"Oh, it just doesn't seem like it's actually been three and a half hours since we got here. Where are the bathrooms?"

Toothless couldn't help but notice the slur in that last sentence. Toothless pointed towards the restrooms, and when Hiccup stood up he had to cling to the table for dear life. Now Toothless was really concerned.

"Hiccup, are you ok?" Toothless asked with genuine concern. He'd had a feeling that he should have cut Hiccup off earlier, and now he realized he should have. There was no way that stick of a boy could keep up with the number of drinks Toothless was having, but he had been matching him all night.

"Yeah, I'm fine," Hiccup said, but Toothless barely understood through the slur. Even Hiccup knew something was wrong at this point, he just didn't want to admit it. He should have listened to Toothless and watched how much he drank.

Hiccup started to walk towards the bathrooms, and that was when Toothless knew for sure something was wrong. He had never seen anyone stagger that badly before. How on earth had Hiccup managed to hide it so well up until this one point?

As Hiccup continued his trek to the bathrooms, he didn't notice Toothless get up from the table and start to slowly follow him. Hiccup also didn't notice anything special in the last moment before he stumbled, vomited, and blacked out.

* * *

**Don't drink too much kids! Seriously, you won't know it's too late until it's too late. You'll feel fine one second, but there'll be one sip that'll send you over the edge. And sometimes that feeling comes all at once, just like it did for poor Hiccup here. You do it once and you will NEVER do it again.**

**Next chapter: On or before November 18**

**The best way to help a hangover is water. And lots of it. For every review, Toothless gets Hiccup to drink a glass. Help Hiccup out, won't you?**


End file.
